SE457534B - Bis-(trimetafan)-nitroprussiat, foerfarande foer dess framstaellning samt farmaceutiska preparat innehaallande naemnda foerening - Google Patents
Bis-(trimetafan)-nitroprussiat, foerfarande foer dess framstaellning samt farmaceutiska preparat innehaallande naemnda foereningInfo
- Publication number
- SE457534B SE457534B SE8300322A SE8300322A SE457534B SE 457534 B SE457534 B SE 457534B SE 8300322 A SE8300322 A SE 8300322A SE 8300322 A SE8300322 A SE 8300322A SE 457534 B SE457534 B SE 457534B
- Authority
- SE
- Sweden
- Prior art keywords
- solution
- preparation
- infusion
- pharmaceutical preparations
- trimethaphane
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 36
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 64
- 239000000243 solution Substances 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 39
- 238000001802 infusion Methods 0.000 claims description 29
- 239000003978 infusion fluid Substances 0.000 claims description 25
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000013543 active substance Substances 0.000 claims description 14
- 239000011550 stock solution Substances 0.000 claims description 13
- 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 claims description 12
- 230000036772 blood pressure Effects 0.000 claims description 12
- 239000008103 glucose Substances 0.000 claims description 12
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 12
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 claims description 12
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 11
- 235000002639 sodium chloride Nutrition 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000004133 Sodium thiosulphate Substances 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 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 claims description 5
- 150000004686 pentahydrates Chemical class 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000002504 physiological saline solution Substances 0.000 claims description 2
- 230000000304 vasodilatating effect Effects 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 229960002460 nitroprusside Drugs 0.000 claims 1
- -1 nitroprusside ion Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- BQMKAHQKDSZAIQ-UHFFFAOYSA-N tetrasodium;iron(3+);nitroxyl anion;pentacyanide Chemical compound [Na+].[Na+].[Na+].[Na+].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].O=[N-] BQMKAHQKDSZAIQ-UHFFFAOYSA-N 0.000 description 28
- 239000003708 ampul Substances 0.000 description 19
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 208000029039 cyanide poisoning Diseases 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 210000002381 plasma Anatomy 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 206010043087 Tachyphylaxis Diseases 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000000729 antidote Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 208000032529 Accidental overdose Diseases 0.000 description 1
- 102000005862 Angiotensin II Human genes 0.000 description 1
- 101800000733 Angiotensin-2 Proteins 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 102100028255 Renin Human genes 0.000 description 1
- 108090000783 Renin Proteins 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 206010046555 Urinary retention Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 208000005946 Xerostomia Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 231100000136 action limit Toxicity 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- 229950006323 angiotensin ii Drugs 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 201000000255 cycloplegia Diseases 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- FGRVOLIFQGXPCT-UHFFFAOYSA-L dipotassium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [K+].[K+].[O-]S([O-])(=O)=S FGRVOLIFQGXPCT-UHFFFAOYSA-L 0.000 description 1
- XEYBHCRIKKKOSS-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide Chemical compound [Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N XEYBHCRIKKKOSS-UHFFFAOYSA-N 0.000 description 1
- XRKMNJXYOFSTBE-UHFFFAOYSA-N disodium;iron(4+);nitroxyl anion;pentacyanide;dihydrate Chemical compound O.O.[Na+].[Na+].[Fe+4].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].O=[N-] XRKMNJXYOFSTBE-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 206010013781 dry mouth Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003457 ganglion blocking agent Substances 0.000 description 1
- 238000011902 gastrointestinal surgery Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 208000031169 hemorrhagic disease Diseases 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 210000000192 parasympathetic ganglia Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000001034 respiratory center Anatomy 0.000 description 1
- 230000035806 respiratory chain Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 235000019187 sodium-L-ascorbate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- CHQOEHPMXSHGCL-UHFFFAOYSA-N trimethaphan Chemical compound C12C[S+]3CCCC3C2N(CC=2C=CC=CC=2)C(=O)N1CC1=CC=CC=C1 CHQOEHPMXSHGCL-UHFFFAOYSA-N 0.000 description 1
- 229940035742 trimethaphan Drugs 0.000 description 1
- HALWUDBBYKMYPW-STOWLHSFSA-M trimethaphan camsylate Chemical compound C1C[C@@]2(CS([O-])(=O)=O)C(=O)C[C@@H]1C2(C)C.C12C[S+]3CCCC3C2N(CC=2C=CC=CC=2)C(=O)N1CC1=CC=CC=C1 HALWUDBBYKMYPW-STOWLHSFSA-M 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH38982 | 1982-01-22 | ||
| CH38882 | 1982-01-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8300322D0 SE8300322D0 (sv) | 1983-01-21 |
| SE8300322L SE8300322L (sv) | 1983-07-23 |
| SE457534B true SE457534B (sv) | 1989-01-09 |
Family
ID=25684424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8300322A SE457534B (sv) | 1982-01-22 | 1983-01-21 | Bis-(trimetafan)-nitroprussiat, foerfarande foer dess framstaellning samt farmaceutiska preparat innehaallande naemnda foerening |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US4740506A (de) |
| AT (1) | AT380882B (de) |
| AU (1) | AU565201B2 (de) |
| CA (1) | CA1222949A (de) |
| DE (1) | DE3301134A1 (de) |
| DK (1) | DK24983A (de) |
| FR (1) | FR2520361B1 (de) |
| GB (1) | GB2113683B (de) |
| IE (1) | IE54429B1 (de) |
| IT (1) | IT1163022B (de) |
| LU (1) | LU84591A1 (de) |
| NL (1) | NL8300184A (de) |
| NZ (1) | NZ203038A (de) |
| SE (1) | SE457534B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1209579B (it) * | 1984-08-08 | 1989-08-30 | Macario Varese As | Impianto per lo smistamento di colli, con carrelli a movimentazione autonoma. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3687967A (en) * | 1969-02-24 | 1972-08-29 | Hoffmann La Roche | {60 -dehydrobiotin synthesis |
| US3957794A (en) * | 1975-05-02 | 1976-05-18 | Hoffmann-La Roche Inc. | 3-Amino-2,3,3a,6,7,7a-hexahydro-thieno[3,2-b]pyridin-(4H)5-one |
-
1983
- 1983-01-06 US US06/456,128 patent/US4740506A/en not_active Expired - Lifetime
- 1983-01-14 DE DE19833301134 patent/DE3301134A1/de not_active Withdrawn
- 1983-01-17 AU AU10513/83A patent/AU565201B2/en not_active Ceased
- 1983-01-17 IT IT19137/83A patent/IT1163022B/it active
- 1983-01-17 NZ NZ203038A patent/NZ203038A/en unknown
- 1983-01-18 NL NL8300184A patent/NL8300184A/nl not_active Application Discontinuation
- 1983-01-20 LU LU84591A patent/LU84591A1/de unknown
- 1983-01-20 FR FR8300876A patent/FR2520361B1/fr not_active Expired
- 1983-01-21 SE SE8300322A patent/SE457534B/sv not_active IP Right Cessation
- 1983-01-21 IE IE120/83A patent/IE54429B1/en unknown
- 1983-01-21 AT AT0020683A patent/AT380882B/de not_active IP Right Cessation
- 1983-01-21 DK DK24983A patent/DK24983A/da not_active Application Discontinuation
- 1983-01-21 CA CA000419966A patent/CA1222949A/en not_active Expired
- 1983-01-21 GB GB08301743A patent/GB2113683B/en not_active Expired
-
1984
- 1984-07-23 US US06/633,243 patent/US4721707A/en not_active Expired - Lifetime
-
1986
- 1986-05-12 US US06/861,853 patent/US4822784A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DK24983A (da) | 1983-07-23 |
| DE3301134A1 (de) | 1983-07-28 |
| US4740506A (en) | 1988-04-26 |
| ATA20683A (de) | 1985-12-15 |
| NZ203038A (en) | 1986-11-12 |
| SE8300322D0 (sv) | 1983-01-21 |
| IE830120L (en) | 1983-07-22 |
| GB2113683B (en) | 1986-01-08 |
| DK24983D0 (da) | 1983-01-21 |
| SE8300322L (sv) | 1983-07-23 |
| FR2520361A1 (fr) | 1983-07-29 |
| IT8319137A0 (it) | 1983-01-17 |
| GB8301743D0 (en) | 1983-02-23 |
| NL8300184A (nl) | 1983-08-16 |
| LU84591A1 (de) | 1984-10-24 |
| US4822784A (en) | 1989-04-18 |
| IE54429B1 (en) | 1989-10-11 |
| US4721707A (en) | 1988-01-26 |
| GB2113683A (en) | 1983-08-10 |
| FR2520361B1 (fr) | 1986-09-05 |
| AU565201B2 (en) | 1987-09-10 |
| AU1051383A (en) | 1983-07-28 |
| CA1222949A (en) | 1987-06-16 |
| AT380882B (de) | 1986-07-25 |
| IT1163022B (it) | 1987-04-08 |
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