SU1251800A3 - Способ получени производных 2-пирролин-3-карбонитрила или их кислотно-аддитивных солей - Google Patents
Способ получени производных 2-пирролин-3-карбонитрила или их кислотно-аддитивных солей Download PDFInfo
- Publication number
- SU1251800A3 SU1251800A3 SU843737938A SU3737938A SU1251800A3 SU 1251800 A3 SU1251800 A3 SU 1251800A3 SU 843737938 A SU843737938 A SU 843737938A SU 3737938 A SU3737938 A SU 3737938A SU 1251800 A3 SU1251800 A3 SU 1251800A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- volume
- pyrroline
- oxo
- carbonitrile
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract description 7
- 150000003839 salts Chemical class 0.000 title abstract description 3
- IFYAGUQDPOGTPG-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrole-4-carbonitrile Chemical class N#CC1=CNCC1 IFYAGUQDPOGTPG-UHFFFAOYSA-N 0.000 title 1
- 239000000654 additive Substances 0.000 title 1
- 239000000126 substance Substances 0.000 claims description 11
- 238000002474 experimental method Methods 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- 238000012360 testing method Methods 0.000 claims description 8
- 210000002683 foot Anatomy 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 241000700159 Rattus Species 0.000 claims description 5
- 235000010418 carrageenan Nutrition 0.000 claims description 5
- 229920001525 carrageenan Polymers 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 210000000548 hind-foot Anatomy 0.000 claims description 4
- 238000005303 weighing Methods 0.000 claims description 4
- 229920000609 methyl cellulose Polymers 0.000 claims description 3
- 239000001923 methylcellulose Substances 0.000 claims description 3
- 230000037396 body weight Effects 0.000 claims description 2
- 230000002497 edematous effect Effects 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 29
- 239000000203 mixture Substances 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 239000003705 antithrombocytic agent Substances 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 230000001732 thrombotic effect Effects 0.000 abstract 1
- -1 3-morpholinopropyl Chemical group 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000004623 platelet-rich plasma Anatomy 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- VFLQQZCRHPIGJU-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine;hydron;chloride Chemical compound Cl.ClCCN1CCCCC1 VFLQQZCRHPIGJU-UHFFFAOYSA-N 0.000 description 1
- WWKHOLGVGCCHGG-UHFFFAOYSA-N 1-[2-(diethylamino)ethyl]-5-oxo-4,4-diphenyl-2-propan-2-ylsulfanylpyrrole-3-carbonitrile Chemical compound N#CC1=C(SC(C)C)N(CCN(CC)CC)C(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 WWKHOLGVGCCHGG-UHFFFAOYSA-N 0.000 description 1
- YFBQXUGQIFAFMM-UHFFFAOYSA-N 2-chloro-n-methylethanamine Chemical compound CNCCCl YFBQXUGQIFAFMM-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- HBVLOSKCMXPFQO-UHFFFAOYSA-N 2-ethylsulfanyl-5-oxo-4,4-diphenyl-1-(3-piperidin-1-ylpropyl)pyrrole-3-carbonitrile;oxalic acid Chemical compound OC(=O)C(O)=O.CCSC1=C(C#N)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C(=O)N1CCCN1CCCCC1 HBVLOSKCMXPFQO-UHFFFAOYSA-N 0.000 description 1
- FQRZVEABMHCOQU-UHFFFAOYSA-N 2-ethylsulfanyl-5-oxo-4,4-diphenyl-1h-pyrrole-3-carbonitrile Chemical compound O=C1NC(SCC)=C(C#N)C1(C=1C=CC=CC=1)C1=CC=CC=C1 FQRZVEABMHCOQU-UHFFFAOYSA-N 0.000 description 1
- STKWICSNFDLOJO-UHFFFAOYSA-N 2-methylsulfanyl-1-(3-morpholin-4-ylpropyl)-5-oxo-4,4-diphenylpyrrole-3-carbonitrile Chemical compound CSC1=C(C#N)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C(=O)N1CCCN1CCOCC1 STKWICSNFDLOJO-UHFFFAOYSA-N 0.000 description 1
- RIGWVWIQEXVOSI-UHFFFAOYSA-N 2-methylsulfanyl-5-oxo-4,4-diphenyl-1-(2-pyrrolidin-1-ylethyl)pyrrole-3-carbonitrile Chemical compound CSC1=C(C#N)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C(=O)N1CCN1CCCC1 RIGWVWIQEXVOSI-UHFFFAOYSA-N 0.000 description 1
- MURJOCYLUBICMW-UHFFFAOYSA-N 2-methylsulfanyl-5-oxo-4,4-diphenyl-1-(3-piperidin-1-ylpropyl)pyrrole-3-carbonitrile Chemical compound CSC1=C(C#N)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C(=O)N1CCCN1CCCCC1 MURJOCYLUBICMW-UHFFFAOYSA-N 0.000 description 1
- LJQNMDZRCXJETK-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.CN(C)CCCCl LJQNMDZRCXJETK-UHFFFAOYSA-N 0.000 description 1
- IWYRLHBVWYZYHF-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]-1-[3-(dimethylamino)propyl]-2-methylsulfanyl-5-oxo-4-pyridin-3-ylpyrrole-3-carbonitrile Chemical compound O=C1N(CCCN(C)C)C(SC)=C(C#N)C1(C=1C=NC=CC=1)C1=CC=C(N(C)C)C=C1 IWYRLHBVWYZYHF-UHFFFAOYSA-N 0.000 description 1
- XQLBAXXPUXQZRZ-UHFFFAOYSA-N 5-oxo-4,4-diphenyl-2-propan-2-ylsulfanyl-1h-pyrrole-3-carbonitrile Chemical compound O=C1NC(SC(C)C)=C(C#N)C1(C=1C=CC=CC=1)C1=CC=CC=C1 XQLBAXXPUXQZRZ-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 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
- 241000699670 Mus sp. Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003236 pyrrolines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 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
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833317653 DE3317653A1 (de) | 1983-05-14 | 1983-05-14 | 2-alkylthio-1-aminoalkyl-2-pyrrolin-3-carbonitrile, verfahren zu deren herstellung sowie deren verwendung bei der prophylaxe und therapie thrombotischer zustaende |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1251800A3 true SU1251800A3 (ru) | 1986-08-15 |
Family
ID=6199021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU843737938A SU1251800A3 (ru) | 1983-05-14 | 1984-05-11 | Способ получени производных 2-пирролин-3-карбонитрила или их кислотно-аддитивных солей |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4499089A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0125684B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS59212469A (cg-RX-API-DMAC7.html) |
| AT (1) | ATE28189T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2798884A (cg-RX-API-DMAC7.html) |
| CS (1) | CS244815B2 (cg-RX-API-DMAC7.html) |
| DD (1) | DD222305A5 (cg-RX-API-DMAC7.html) |
| DE (2) | DE3317653A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK239084A (cg-RX-API-DMAC7.html) |
| ES (3) | ES532438A0 (cg-RX-API-DMAC7.html) |
| GR (1) | GR82094B (cg-RX-API-DMAC7.html) |
| HU (1) | HUT34158A (cg-RX-API-DMAC7.html) |
| SU (1) | SU1251800A3 (cg-RX-API-DMAC7.html) |
| YU (1) | YU83284A (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA843615B (cg-RX-API-DMAC7.html) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL176372B (nl) * | 1952-02-26 | Salvat Editores | Werkwijze voor het bereiden van drukinkt alsmede werkwijze voor het bereiden van een preparaat om aan drukinkt te worden toegevoegd. | |
| FI59246C (fi) * | 1974-06-24 | 1981-07-10 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av benscykloamidderivat anvaendbara vid trombos- och emboliterapin |
| NZ182264A (en) * | 1975-10-25 | 1979-01-11 | Beecham Group Ltd | 2-carboxyalkyl-1-hydroxyalkyl-pyrrolidin-3,5-dione or-piperidin-3,6-dione derivatives prarmaceutical compostions |
| US4329347A (en) * | 1978-02-17 | 1982-05-11 | Boehringer Ingelheim Gmbh | Cardiotonic and antithrombotic sulfur-containing derivatives of carbostyril |
| DK75779A (da) * | 1978-03-13 | 1979-09-14 | Du Pont | 4,5-diaryl-2- (substitueret thio) pyrroler og sulfoxider og sulfoner deraf samt fremgangsmaader til deres fremstilling og anvendelse |
| DE3212591A1 (de) * | 1982-04-03 | 1983-10-13 | Gödecke AG, 1000 Berlin | 2-pyrrolin-3-carbonitril-derivate, verfahren zu deren herstellung und diese enthaltende arzneimittel |
-
1983
- 1983-05-14 DE DE19833317653 patent/DE3317653A1/de not_active Ceased
-
1984
- 1984-05-04 CS CS843308A patent/CS244815B2/cs unknown
- 1984-05-10 GR GR74677A patent/GR82094B/el unknown
- 1984-05-10 US US06/608,828 patent/US4499089A/en not_active Expired - Fee Related
- 1984-05-11 HU HU841851A patent/HUT34158A/hu unknown
- 1984-05-11 DD DD84262957A patent/DD222305A5/de unknown
- 1984-05-11 JP JP59093126A patent/JPS59212469A/ja active Pending
- 1984-05-11 YU YU00832/84A patent/YU83284A/xx unknown
- 1984-05-11 SU SU843737938A patent/SU1251800A3/ru active
- 1984-05-11 ES ES532438A patent/ES532438A0/es active Granted
- 1984-05-11 ES ES532445A patent/ES532445A0/es active Granted
- 1984-05-11 ES ES532446A patent/ES8502421A1/es not_active Expired
- 1984-05-14 AU AU27988/84A patent/AU2798884A/en not_active Abandoned
- 1984-05-14 EP EP84105457A patent/EP0125684B1/de not_active Expired
- 1984-05-14 DK DK239084A patent/DK239084A/da not_active Application Discontinuation
- 1984-05-14 ZA ZA843615A patent/ZA843615B/xx unknown
- 1984-05-14 DE DE8484105457T patent/DE3464601D1/de not_active Expired
- 1984-05-14 AT AT84105457T patent/ATE28189T1/de not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| Rompps Chemie-Lexikon,. 6-е издание, т. III, 1966, с. 4849, и 7-е издание, т. III, 1973, с. 1588. * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3464601D1 (en) | 1987-08-13 |
| ES532446A0 (es) | 1985-01-01 |
| ES8502867A1 (es) | 1985-02-01 |
| EP0125684B1 (de) | 1987-07-08 |
| ZA843615B (en) | 1984-12-24 |
| CS244815B2 (en) | 1986-08-14 |
| ES532438A0 (es) | 1985-02-01 |
| DD222305A5 (de) | 1985-05-15 |
| ES8502868A1 (es) | 1985-02-01 |
| DK239084A (da) | 1984-11-15 |
| HUT34158A (en) | 1985-02-28 |
| ES532445A0 (es) | 1985-02-01 |
| ATE28189T1 (de) | 1987-07-15 |
| DK239084D0 (da) | 1984-05-14 |
| EP0125684A1 (de) | 1984-11-21 |
| ES8502421A1 (es) | 1985-01-01 |
| AU2798884A (en) | 1984-11-15 |
| GR82094B (cg-RX-API-DMAC7.html) | 1984-12-13 |
| JPS59212469A (ja) | 1984-12-01 |
| YU83284A (en) | 1986-10-31 |
| DE3317653A1 (de) | 1984-11-15 |
| CS330884A2 (en) | 1985-09-17 |
| US4499089A (en) | 1985-02-12 |
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