AT516070B1 - Verfahren zur Herstellung von Polyguanidinen - Google Patents
Verfahren zur Herstellung von Polyguanidinen Download PDFInfo
- Publication number
- AT516070B1 AT516070B1 ATA609/2014A AT6092014A AT516070B1 AT 516070 B1 AT516070 B1 AT 516070B1 AT 6092014 A AT6092014 A AT 6092014A AT 516070 B1 AT516070 B1 AT 516070B1
- Authority
- AT
- Austria
- Prior art keywords
- polyguanidine
- guanidine
- aromatic ring
- aminoguanidine
- gua
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 43
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 22
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 22
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- -1 guanidinediyl Chemical group 0.000 claims abstract description 16
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 16
- FQQQSNAVVZSYMB-UHFFFAOYSA-N 1,1-diaminoguanidine Chemical compound NN(N)C(N)=N FQQQSNAVVZSYMB-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000001743 benzylic group Chemical group 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 13
- 230000008030 elimination Effects 0.000 claims abstract description 11
- 238000003379 elimination reaction Methods 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 230000000845 anti-microbial effect Effects 0.000 claims description 10
- 230000003115 biocidal effect Effects 0.000 claims description 8
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 208000035143 Bacterial infection Diseases 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical class C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 6
- 239000004305 biphenyl Chemical class 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 239000004599 antimicrobial Substances 0.000 claims description 5
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical class C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229930192474 thiophene Chemical class 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000007910 systemic administration Methods 0.000 claims description 2
- 238000011200 topical administration Methods 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 229960004198 guanidine Drugs 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- 150000004985 diamines Chemical class 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 150000002357 guanidines Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 150000002829 nitrogen Chemical class 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- UBDZFAGVPPMTIT-UHFFFAOYSA-N 2-aminoguanidine;hydron;chloride Chemical compound [Cl-].NC(N)=N[NH3+] UBDZFAGVPPMTIT-UHFFFAOYSA-N 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003139 biocide Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GRJWOKACBGZOKT-UHFFFAOYSA-N 1,3-bis(chloromethyl)benzene Chemical group ClCC1=CC=CC(CCl)=C1 GRJWOKACBGZOKT-UHFFFAOYSA-N 0.000 description 2
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 2
- YOOSAIJKYCBPFW-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)butoxy]propan-1-amine Chemical compound NCCCOCCCCOCCCN YOOSAIJKYCBPFW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- JGGFDEJXWLAQKR-UHFFFAOYSA-N 1,2-diaminoguanidine Chemical group NNC(N)=NN JGGFDEJXWLAQKR-UHFFFAOYSA-N 0.000 description 1
- HAZRIBSLCUYMQP-UHFFFAOYSA-N 1,2-diaminoguanidine;hydron;chloride Chemical compound Cl.NN\C(N)=N/N HAZRIBSLCUYMQP-UHFFFAOYSA-N 0.000 description 1
- OXHOPZLBSSTTBU-UHFFFAOYSA-N 1,3-bis(bromomethyl)benzene Chemical group BrCC1=CC=CC(CBr)=C1 OXHOPZLBSSTTBU-UHFFFAOYSA-N 0.000 description 1
- RBZMSGOBSOCYHR-UHFFFAOYSA-N 1,4-bis(bromomethyl)benzene Chemical group BrCC1=CC=C(CBr)C=C1 RBZMSGOBSOCYHR-UHFFFAOYSA-N 0.000 description 1
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical group ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- JUNBYRXGWOTEEP-UHFFFAOYSA-N [C].NC(N)=N Chemical group [C].NC(N)=N JUNBYRXGWOTEEP-UHFFFAOYSA-N 0.000 description 1
- FUASJQSBFUVWJQ-UHFFFAOYSA-N [N].NC(N)=N Chemical compound [N].NC(N)=N FUASJQSBFUVWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001142 anti-diarrhea Effects 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 238000011482 antibacterial activity assay Methods 0.000 description 1
- 238000009635 antibiotic susceptibility testing Methods 0.000 description 1
- 229940125714 antidiarrheal agent Drugs 0.000 description 1
- 239000003793 antidiarrheal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 238000012458 antifungal assay Methods 0.000 description 1
- 238000002827 antifungal susceptibility testing Methods 0.000 description 1
- 229960005475 antiinfective agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- SCIZLHIMZCLSND-UHFFFAOYSA-N diamino(carbamimidoyl)azanium;chloride Chemical compound Cl.NN(N)C(N)=N SCIZLHIMZCLSND-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical class Cl* 0.000 description 1
- 238000007877 drug screening Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000003527 eukaryotic cell Anatomy 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000007704 transition Effects 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
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/16—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- 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
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/43—Guanidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0627—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Polymers & Plastics (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Birds (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Paints Or Removers (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Compounds Of Unknown Constitution (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ATA609/2014A AT516070B1 (de) | 2014-07-31 | 2014-07-31 | Verfahren zur Herstellung von Polyguanidinen |
| SG11201700749VA SG11201700749VA (en) | 2014-07-31 | 2015-07-30 | Method for producing polyguanidines |
| PT15771843T PT3174848T (pt) | 2014-07-31 | 2015-07-30 | Processo para a preparação de poliguanidinas |
| AU2015296881A AU2015296881B2 (en) | 2014-07-31 | 2015-07-30 | Method for producing polyguanidines |
| BR112017002094-7A BR112017002094B1 (pt) | 2014-07-31 | 2015-07-30 | Método para produção de poliguanidinas |
| HUE15771843A HUE041586T2 (hu) | 2014-07-31 | 2015-07-30 | Eljárás poliguanidinek elõállítására |
| EP15771843.8A EP3174848B1 (de) | 2014-07-31 | 2015-07-30 | Verfahren zur herstellung von polyguanidinen |
| US15/500,772 US10335431B2 (en) | 2014-07-31 | 2015-07-30 | Method for producing polyguanidines |
| HRP20181805TT HRP20181805T1 (hr) | 2014-07-31 | 2015-07-30 | Postupak za proizvodnju poligvanidina |
| TR2018/16160T TR201816160T4 (en) | 2014-07-31 | 2015-07-30 | PRODUCTION PROCEDURE OF POLYGUANIDINS. |
| EA201790249A EA035565B1 (ru) | 2014-07-31 | 2015-07-30 | Способ получения полигуанидина |
| ES15771843T ES2699185T3 (es) | 2014-07-31 | 2015-07-30 | Procedimiento para la preparación de poliguanidinas |
| PL15771843T PL3174848T3 (pl) | 2014-07-31 | 2015-07-30 | Sposób wytwarzania poliguanidyn |
| MYPI2017700328A MY186388A (en) | 2014-07-31 | 2015-07-30 | Method for producing polyguanidines |
| PCT/AT2015/050187 WO2016015081A1 (de) | 2014-07-31 | 2015-07-30 | Verfahren zur herstellung von polyguanidinen |
| SI201530459T SI3174848T1 (sl) | 2014-07-31 | 2015-07-30 | Postopek za pripravo poligvanidinov |
| CN201580051065.1A CN106715387B (zh) | 2014-07-31 | 2015-07-30 | 制备聚胍的方法 |
| JP2017505529A JP6723221B2 (ja) | 2014-07-31 | 2015-07-30 | ポリグアニジンの製造方法 |
| DK15771843.8T DK3174848T3 (en) | 2014-07-31 | 2015-07-30 | Process for the preparation of polyguanidines |
| PH12017500186A PH12017500186B1 (en) | 2014-07-31 | 2017-01-31 | Method for producing polyguanidines |
| CY20181101138T CY1121425T1 (el) | 2014-07-31 | 2018-11-01 | Μεθοδος για την παρασκευη πολυγουανιδινων |
| US16/411,703 US11013760B2 (en) | 2014-07-31 | 2019-05-14 | Polyguanidine polymers and methods of use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ATA609/2014A AT516070B1 (de) | 2014-07-31 | 2014-07-31 | Verfahren zur Herstellung von Polyguanidinen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AT516070A1 AT516070A1 (de) | 2016-02-15 |
| AT516070B1 true AT516070B1 (de) | 2016-08-15 |
Family
ID=54238154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ATA609/2014A AT516070B1 (de) | 2014-07-31 | 2014-07-31 | Verfahren zur Herstellung von Polyguanidinen |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US10335431B2 (enExample) |
| EP (1) | EP3174848B1 (enExample) |
| JP (1) | JP6723221B2 (enExample) |
| CN (1) | CN106715387B (enExample) |
| AT (1) | AT516070B1 (enExample) |
| AU (1) | AU2015296881B2 (enExample) |
| BR (1) | BR112017002094B1 (enExample) |
| CY (1) | CY1121425T1 (enExample) |
| DK (1) | DK3174848T3 (enExample) |
| EA (1) | EA035565B1 (enExample) |
| ES (1) | ES2699185T3 (enExample) |
| HR (1) | HRP20181805T1 (enExample) |
| HU (1) | HUE041586T2 (enExample) |
| MY (1) | MY186388A (enExample) |
| PH (1) | PH12017500186B1 (enExample) |
| PL (1) | PL3174848T3 (enExample) |
| PT (1) | PT3174848T (enExample) |
| SG (1) | SG11201700749VA (enExample) |
| SI (1) | SI3174848T1 (enExample) |
| TR (1) | TR201816160T4 (enExample) |
| WO (1) | WO2016015081A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6703140B2 (ja) * | 2017-01-13 | 2020-06-03 | 三井化学株式会社 | 抗菌性材料及びその応用 |
| US11166464B2 (en) * | 2017-03-06 | 2021-11-09 | The United States Of America, As Represented By The Secretary Of Agriculture | Self-assembled active agents |
| EP3524055A1 (de) | 2018-02-08 | 2019-08-14 | BCSK Biocid GmbH | Antibakterielles und spermizides gleitmittel |
| AT521124A1 (de) * | 2018-03-23 | 2019-10-15 | Bcsk Biocid Gmbh | Verfahren und Zusammensetzung zur Bekämpfung von Viren der Familie Picornaviridae |
| CN113527672B (zh) * | 2020-03-30 | 2022-09-20 | 复旦大学 | 一种胍基衍生物及其基因递释系统 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1095902A (en) * | 1964-04-09 | 1967-12-20 | Sterling Drug Inc | Guanidine derivatives |
| EP0619272A1 (en) * | 1993-04-05 | 1994-10-12 | Agfa-Gevaert N.V. | Method for the purification of waste water containing silver |
| JP2001271293A (ja) * | 2000-03-22 | 2001-10-02 | Nicca Chemical Co Ltd | 抗菌性紙製品 |
| EP1172224A1 (en) * | 1999-03-29 | 2002-01-16 | Nicca Chemical Co., Ltd. | Substrate of recording |
| FR2827507A1 (fr) * | 2001-07-18 | 2003-01-24 | Oreal | Compose derive de polyguanidine et utilisation d'un tel compose pour la protection et/ou le soin des fibres keratiniques |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2325586A (en) * | 1940-03-21 | 1943-08-03 | Du Pont | Polymeric guanidines and process for preparing the same |
| BE553517A (enExample) | 1955-12-19 | |||
| US3700697A (en) * | 1968-04-22 | 1972-10-24 | Sterling Drug Inc | (2,3-dihydro-2-benzofuranylmethyl) guanidines and their preparation |
| JPS4926320B1 (enExample) * | 1970-08-29 | 1974-07-08 | ||
| US3901944A (en) * | 1972-05-08 | 1975-08-26 | American Cyanamid Co | 1,3-bis(substituted benzylideneamino)guanidines |
| CA2408191C (en) * | 2000-05-11 | 2006-11-14 | P.O.C. Oil Industry Technology Beratungsges.M.B.H. | Biocidal polymers based on guanidine salts |
| AT500998B1 (de) * | 2003-03-20 | 2008-10-15 | Geopharma Produktionsgmbh | Antimikrobiell wirkendes arzneimittel |
| CN100406496C (zh) * | 2003-07-23 | 2008-07-30 | 上海塑杰科技有限公司 | 一种多元胺与胍盐聚合物及其在抗菌聚酯和聚酰胺材料中的应用 |
| JP2007502883A (ja) * | 2003-08-18 | 2007-02-15 | エスケー ケミカルズ カンパニー リミテッド | ポリアルキレンバイグアニジン塩の製造方法 |
| KR20050019173A (ko) * | 2003-08-18 | 2005-03-03 | 에스케이케미칼주식회사 | 폴리알킬렌바이구아니딘염의 제조 방법 |
-
2014
- 2014-07-31 AT ATA609/2014A patent/AT516070B1/de not_active IP Right Cessation
-
2015
- 2015-07-30 WO PCT/AT2015/050187 patent/WO2016015081A1/de not_active Ceased
- 2015-07-30 BR BR112017002094-7A patent/BR112017002094B1/pt not_active IP Right Cessation
- 2015-07-30 US US15/500,772 patent/US10335431B2/en active Active
- 2015-07-30 SI SI201530459T patent/SI3174848T1/sl unknown
- 2015-07-30 PT PT15771843T patent/PT3174848T/pt unknown
- 2015-07-30 PL PL15771843T patent/PL3174848T3/pl unknown
- 2015-07-30 HU HUE15771843A patent/HUE041586T2/hu unknown
- 2015-07-30 JP JP2017505529A patent/JP6723221B2/ja not_active Expired - Fee Related
- 2015-07-30 TR TR2018/16160T patent/TR201816160T4/en unknown
- 2015-07-30 AU AU2015296881A patent/AU2015296881B2/en not_active Ceased
- 2015-07-30 ES ES15771843T patent/ES2699185T3/es active Active
- 2015-07-30 DK DK15771843.8T patent/DK3174848T3/en active
- 2015-07-30 SG SG11201700749VA patent/SG11201700749VA/en unknown
- 2015-07-30 HR HRP20181805TT patent/HRP20181805T1/hr unknown
- 2015-07-30 MY MYPI2017700328A patent/MY186388A/en unknown
- 2015-07-30 CN CN201580051065.1A patent/CN106715387B/zh not_active Expired - Fee Related
- 2015-07-30 EA EA201790249A patent/EA035565B1/ru unknown
- 2015-07-30 EP EP15771843.8A patent/EP3174848B1/de active Active
-
2017
- 2017-01-31 PH PH12017500186A patent/PH12017500186B1/en unknown
-
2018
- 2018-11-01 CY CY20181101138T patent/CY1121425T1/el unknown
-
2019
- 2019-05-14 US US16/411,703 patent/US11013760B2/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1095902A (en) * | 1964-04-09 | 1967-12-20 | Sterling Drug Inc | Guanidine derivatives |
| EP0619272A1 (en) * | 1993-04-05 | 1994-10-12 | Agfa-Gevaert N.V. | Method for the purification of waste water containing silver |
| EP1172224A1 (en) * | 1999-03-29 | 2002-01-16 | Nicca Chemical Co., Ltd. | Substrate of recording |
| JP2001271293A (ja) * | 2000-03-22 | 2001-10-02 | Nicca Chemical Co Ltd | 抗菌性紙製品 |
| FR2827507A1 (fr) * | 2001-07-18 | 2003-01-24 | Oreal | Compose derive de polyguanidine et utilisation d'un tel compose pour la protection et/ou le soin des fibres keratiniques |
Non-Patent Citations (1)
| Title |
|---|
| Wei, Dafu et al. "Condensation between guanidine hydrochloride and diamine/multi-amine and its influence on the structures and antibacterial activity of oligoguanidines" e-Polymers (2012) 072; CODEN: EPOLCI; URL: http://www.e-polymers.org/journal/papers/yguan_260812.pdf. CAPLUS [online] Copyright 2015 ACS on STN [ermittelt am 17.6.2015]. Ermittelt in: STN International, Karlsruhe. Accession No. 2012:1318179 CAPLUS. * |
Also Published As
| Publication number | Publication date |
|---|---|
| SI3174848T1 (sl) | 2019-03-29 |
| AU2015296881B2 (en) | 2020-01-02 |
| US11013760B2 (en) | 2021-05-25 |
| HUE041586T2 (hu) | 2019-05-28 |
| TR201816160T4 (en) | 2018-12-21 |
| ES2699185T3 (es) | 2019-02-07 |
| SG11201700749VA (en) | 2017-02-27 |
| DK3174848T3 (en) | 2018-11-26 |
| PH12017500186A1 (en) | 2017-06-28 |
| PL3174848T3 (pl) | 2019-05-31 |
| CN106715387B (zh) | 2019-07-12 |
| JP2017530211A (ja) | 2017-10-12 |
| PT3174848T (pt) | 2018-11-29 |
| MY186388A (en) | 2021-07-21 |
| CY1121425T1 (el) | 2020-05-29 |
| EP3174848B1 (de) | 2018-08-01 |
| JP6723221B2 (ja) | 2020-07-15 |
| AU2015296881A1 (en) | 2017-02-23 |
| CN106715387A (zh) | 2017-05-24 |
| BR112017002094B1 (pt) | 2023-02-07 |
| US10335431B2 (en) | 2019-07-02 |
| EA201790249A1 (ru) | 2017-07-31 |
| AT516070A1 (de) | 2016-02-15 |
| US20190269719A1 (en) | 2019-09-05 |
| EA035565B1 (ru) | 2020-07-08 |
| US20170224723A1 (en) | 2017-08-10 |
| BR112017002094A2 (pt) | 2017-11-21 |
| EP3174848A1 (de) | 2017-06-07 |
| WO2016015081A1 (de) | 2016-02-04 |
| WO2016015081A9 (de) | 2016-03-31 |
| HRP20181805T1 (hr) | 2019-03-22 |
| PH12017500186B1 (en) | 2019-06-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2948496B1 (de) | Neue bioaktive polymere | |
| EP3174848B1 (de) | Verfahren zur herstellung von polyguanidinen | |
| AT505102B1 (de) | Biozid, insbesondere fungizid wirkendes mittel | |
| EP1280766A1 (de) | Biozide polymere auf der basis von guanidin-salzen | |
| EP2498766A1 (de) | Polymere oder oligomere wirkstoffe mit biozider wirkung, verfahren zu deren herstellung und zusammensetzung umfassend einen polymeren oder oligomeren wirkstoff | |
| EP3194371B1 (en) | Antimicrobial imidazolium compounds | |
| EP1734064B1 (de) | Polymere Guanidinderivate als zytostatische Arzneimittel | |
| DE112011104690T5 (de) | Nichtionisches N-Vinylbutyrolactam-Iod mit hoher Stabilität und dessen Herstellungsverfahren | |
| DE102009060249B4 (de) | Verfahren zur Herstellung des Desinfektionsmittels Polyhexamethylenguanidinhydroiodid | |
| EP2654740B1 (de) | Antibakteriell und antimykotisch wirkende biphenylyl-verbindungen | |
| DE69910810T2 (de) | Natriumsalz von 3-(4-cinnamyl-1-piperazinyl)-iminomethyl-rifamycin sv und verfahren zu seiner herstellung | |
| AT408302B (de) | Biozide polymere der reihe der polyoxyalkylen-guanidin-hydrochloride und verfahren zu deren herstellung | |
| CH606191A5 (en) | Polymeric quat. ammonium salts derived from bis-halomethyl diphenyl | |
| WO2017148795A1 (de) | Isophthalsäuredichlorid zur erhöhung der lagerstabilität von xylylendiisocyanat | |
| EP3445816A1 (de) | Antimikrobiell wirkende, nicht ausblutende thermoplastische formmassen | |
| CN112933240A (zh) | 超分子聚合物组合物及其制备方法 | |
| AT517496A1 (de) | Polymeres Kondensationsprodukt in Salzform mit Guanidinium-Gruppen und Silikat-Ionen | |
| EP2338342A1 (de) | Polyharnstoff mit bioziden Eigenschaften | |
| DE2433170A1 (de) | Anilinoderivate von chelocardin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM01 | Lapse because of not paying annual fees |
Effective date: 20200731 |