CH550179A - 2-substituted vinyl-5-nitroimidazoles active against - trypanosoma-amdebae and trichomonas - Google Patents
2-substituted vinyl-5-nitroimidazoles active against - trypanosoma-amdebae and trichomonasInfo
- Publication number
- CH550179A CH550179A CH763472A CH763472A CH550179A CH 550179 A CH550179 A CH 550179A CH 763472 A CH763472 A CH 763472A CH 763472 A CH763472 A CH 763472A CH 550179 A CH550179 A CH 550179A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- vinyl
- compound
- trypanosoma
- nitroimidazole
- Prior art date
Links
- -1 2-substituted vinyl-5-nitroimidazoles Chemical class 0.000 title claims abstract description 7
- 241000224526 Trichomonas Species 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 241000223104 Trypanosoma Species 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 150000001408 amides Chemical class 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- QRJGDBPFSOPRCQ-UHFFFAOYSA-N 4-[2-(1-ethenyl-5-nitroimidazol-2-yl)ethenyl]benzaldehyde Chemical compound C=CN1C([N+](=O)[O-])=CN=C1C=CC1=CC=C(C=O)C=C1 QRJGDBPFSOPRCQ-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- AWJPSVDQGUYQSB-UHFFFAOYSA-N 1-ethenyl-2-methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1C=C AWJPSVDQGUYQSB-UHFFFAOYSA-N 0.000 claims description 2
- YNWFBJINYXHJDW-UHFFFAOYSA-N 2-(1,3-dioxolan-2-yl)benzaldehyde Chemical compound O=CC1=CC=CC=C1C1OCCO1 YNWFBJINYXHJDW-UHFFFAOYSA-N 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- XXTKORQHKOYXIH-UHFFFAOYSA-N 4-(1,3-dioxolan-2-yl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1OCCO1 XXTKORQHKOYXIH-UHFFFAOYSA-N 0.000 claims description 2
- RBNZISNWCHORNF-UHFFFAOYSA-N 4-[2-(1-ethenyl-5-nitroimidazol-2-yl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C=CC1=NC=C([N+]([O-])=O)N1C=C RBNZISNWCHORNF-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 241001502500 Trichomonadida Species 0.000 claims description 2
- 241000223109 Trypanosoma cruzi Species 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 230000002141 anti-parasite Effects 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 244000045947 parasite Species 0.000 claims description 2
- 230000009993 protective function Effects 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 abstract 1
- LTZDJIFKBOWWET-UHFFFAOYSA-N 1-ethenyl-5-nitro-2-(2-phenylethenyl)imidazole Chemical compound C=CN1C([N+](=O)[O-])=CN=C1C=CC1=CC=CC=C1 LTZDJIFKBOWWET-UHFFFAOYSA-N 0.000 abstract 1
- 150000004958 5-nitroimidazoles Chemical class 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract 1
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 238000001727 in vivo Methods 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
5-Nitroimidazoles of general formulae (I) and (II): are active in vivo against Amboae, Trichomonas and esp. Trypanosoma. In the above formulae, Ra and Rb independently represent H or C1-C8 alkyl, and R represents one of the following groups: and their alkyl and alkoxy derivatives: CH2NH2 which may be substd. on the NH2 gp. Rc represents H, C1-C8 alkyl, tosyl or brosyl; R1 and R2 represents H, C1-C4 alkyl or when R is other than pyridyl (opt. subst.); R1 and R2 represent H, C1-C8 alkyl, halogen, CF3, nitro, amino or dialkylamino; R3, R4 and R5 represent alkyl, alkoxy, carboxy, formyl, hydroxymethyl or aminoalkyl. (I) cannot represent 1-vinyl-2-styryl-5-nitroimidazole. Preparation of (I) and (II) is by reaction of an aromatic aldehyde RCHO in the presence of a strong base with a compound (III) or (IV).
Description
La présente invention a pour objet un procédé de préparation d'un nouveau composé chimique doué de propriétés antiparasitaires. de formule:
EMI1.1
ainsi que des sels, esters et amides de ce composé. On prépare ce composé par oxydation du l-vinyl-2-(4-formylstyryl)-5-nitro- imidazole. Ce dernier composé peut lui-même être préparé par condensation du 1 -vinyl-2-méthyl-5-nitroimidazole avec du p (1 ,3-dioxa-2-cyclopentyl)benzaldéhyde en présence d'une base forte, suivie d'hydrolyse pour illuminer la fonction protectrice acétal cyclique.
Le procédé d'oxydation cidessus conduit à l'acide carboxylique libre. Cependant, si désiré, on peut isoler le composé de formule I sous forme de sel, ou on peut le transformer en ester. On peut également utiliser l'acide pour la préparation d'amides. Ainsi, on peut obtenir un sel, tel qu'un sel de métal alcalin, par traitement de l'acide libre avec une base telle que l'hydroxyde de sodium, tandis que l'on obtient facilement un ester par réaction de l'acide libre ou de son chlorure ou anhydride d'acide avec un alcool approprié. Pour l'isolement sous forme d'amide, on peut faire réagir l'acide libre avec l'urée, ou on peut faire réagir le chlorure ou l'anhydride ou un ester de l'acide correspondant avec l'ammoniac ou une amine appropriée.
Le composé de formule I et ses sels, esters et amides sont actifs contre certains organismes connus comme parasites de l'homme et des mammifères, en particulier les amides, les trichomonades et la famille Trypanosomidae, spécialement les souches Trypanosoma
Rhodesiense, Trypanosoma Cruzi, Trypanosoma ambiense et Trypanosoma Cogolense.
L'exemple suivant illustre le procédé delon l'invention:
(a) On agite 7,6 g de 1-vinyl-2-méthyl-5-nitroimadazole et 9 g de p-( I ,3-dioxa-2-cyclopentyl)benzaldéhyde dans 30 ml de diméthylsulfoxyde à la température ordinaire et on ajoute rapidement une solution de 3 g de sodium dans 40 ml de méthanol.
Aprés avoir laissé reposer jusqu'au lendemain à la température ordinaire, on dissout le mélange dans du tétrahydrofuranne en chauffant à 40"C et en agitant. On ajoute 2 ml d'eau et I ml d'acide chlorhydrique concentré et on continue à agiter pendant 30 minutes. Aprés avoir refroidi et laissé reposer à la température ordinaire pendant I heure, on recueille les cristaux qui se sont formés et on les recristallise dans de l'acétate d'éthyle, obtenant ainsi le l-vinyl-2-(4-formylstyryl)-5-nitroimidazole, p.f. 196-197' C.
(b) On agite 80 g (0,3 mole) de l-vinyl-2-(4-formylstyryl)-5- nitroimidazole dans 800 ml d'acétone (qualité AR) à la température ordinaire et on ajoute goutte à goutte une solution de 80 ml d'acide chromique 8N en l'espace de 30 minutes. On continue à agiter à la température ordinaire pendant 4 heures. On recueille le solide jaune, on le lave à l'eau chaude et on le sèche sous vide à 60' C. On suspend l'acide brut (73,7 g) dans 1,8 litre d'eau, on agite et on règle au pH constant de 9 en ajoutant avec précaution une solution d'hydroxyde de sodium 4N.
On sépare par centrifugation un solide jaune insoluble très fin, consistant en aldéhyde non transformé en quantité de 9,7 g, p.f. 194-195-C. On agite le centrifugat et on ajoute de l'acide chlorhydrique concentré, goutte à goutte, lentement, jusqu'au pH 3,5. On recueille le solide jaune fin, on le lave à l'eau et on le sèche sous vide à 60 C, obtenant ainsi 58,9 g de l-vinyl-2-(4-carboxystyryl)-5-nitro- imidazole, p.f. 306-308- C (déc.).
Analyse:
Calculé pour C14H11N3O4 C 59,0 H 3,89 N 14,7%
Trouvé C 58,8 H 3.62 N 14,6%
On redissout une partie de l'acide en solution aqueuse par addition de la quantité calculée d'hydroxyde de sodium 4N pour obtenir une solution de pH 8,8. On évapore la solution sous vide jusqu'à un faible volume, on la dilue dans dix fois son volume de n-butanol et on l'évapore à nouveau sous vide, obtenant ainsi des cristaux jaunes que l'on recueille, lave à l'acétone et sèche sous vide à 60"C pour obtenir le sel de sodium.
Analyse:
Calculé pour Cl4Hl0N304Na Na 7,49%
Trouvé Na 7,52% REVENDICATION I
Procédé de préparation du composé de formule:
EMI1.2
caractérisé en ce que l'on oxyde du l-vinyl-2-(4-formylstyryl)-5- nitroimidazole et l'on isole l'acide résultant comme tel ou sous forme d'un sel.
SOUS-REVENDICATIONS
1. Procédé selon la revendication I, caractérisé en ce que l'on effectue l'oxydation au moyen d'acide chromique.
2. Procédé selon la revendication I ou la sous-revendication 1, caractérisé en ce que l'on isole l'acide sous forme de son sel de sodium.
4. Procédé selon la revendication I ou la sous-revendication 1, caractérisé en ce que l'on transforme l'acide obtenu en un ester.
REVENDICATION II
Utilisation de l'acide obtenu conformément au procédé selon la revendication I pour la préparation d'un amide de cet acide.
**ATTENTION** fin du champ DESC peut contenir debut de CLMS **.
The present invention relates to a process for preparing a new chemical compound endowed with antiparasitic properties. of formula:
EMI1.1
as well as salts, esters and amides of this compound. This compound is prepared by oxidation of 1-vinyl-2- (4-formylstyryl) -5-nitroimidazole. The latter compound can itself be prepared by condensation of 1-vinyl-2-methyl-5-nitroimidazole with p (1, 3-dioxa-2-cyclopentyl) benzaldehyde in the presence of a strong base, followed by hydrolysis to illuminate the protective function cyclic acetal.
The above oxidation process results in the free carboxylic acid. However, if desired, the compound of formula I can be isolated as a salt, or it can be made into an ester. The acid can also be used for the preparation of amides. Thus, a salt, such as an alkali metal salt, can be obtained by treating the free acid with a base such as sodium hydroxide, while an ester is easily obtained by reacting the acid. free or its acid chloride or anhydride with a suitable alcohol. For isolation as an amide, the free acid can be reacted with urea, or the chloride or anhydride or an ester of the corresponding acid can be reacted with ammonia or a suitable amine. .
The compound of formula I and its salts, esters and amides are active against certain organisms known to be parasites of humans and mammals, in particular amides, trichomonads and the Trypanosomidae family, especially Trypanosoma strains.
Rhodesiense, Trypanosoma Cruzi, Trypanosoma ambiense and Trypanosoma Cogolense.
The following example illustrates the process of the invention:
(a) 7.6 g of 1-vinyl-2-methyl-5-nitroimadazole and 9 g of p- (I, 3-dioxa-2-cyclopentyl) benzaldehyde are stirred in 30 ml of dimethylsulfoxide at room temperature and quickly add a solution of 3 g of sodium in 40 ml of methanol.
After allowing to stand overnight at room temperature, the mixture is dissolved in tetrahydrofuran with heating to 40 ° C. and stirring. 2 ml of water and 1 ml of concentrated hydrochloric acid are added and stirring is continued. for 30 minutes After having cooled and left to stand at room temperature for 1 hour, the crystals which formed were collected and recrystallized from ethyl acetate, thereby obtaining 1-vinyl-2- (4 -formylstyryl) -5-nitroimidazole, mp 196-197 'C.
(b) 80 g (0.3 mole) of 1-vinyl-2- (4-formylstyryl) -5-nitroimidazole are stirred in 800 ml of acetone (AR grade) at room temperature and a mixture is added dropwise. 80 ml solution of 8N chromic acid over 30 minutes. Stirring is continued at room temperature for 4 hours. The yellow solid was collected, washed with hot water and dried in vacuo at 60 ° C. The crude acid (73.7 g) was suspended in 1.8 liters of water, stirred and carried out. adjust to a constant pH of 9 by carefully adding 4N sodium hydroxide solution.
A very fine insoluble yellow solid consisting of unconverted aldehyde in an amount of 9.7 g, m.p. 194-195-C. The centrifugate is stirred and concentrated hydrochloric acid is added slowly, dropwise, until pH 3.5. The fine yellow solid was collected, washed with water and dried under vacuum at 60 ° C., thus obtaining 58.9 g of 1-vinyl-2- (4-carboxystyryl) -5-nitro-imidazole, m.p. 306-308- C (dec.).
Analysis:
Calculated for C14H11N3O4 C 59.0 H 3.89 N 14.7%
Found C 58.8 H 3.62 N 14.6%
Part of the acid is dissolved in aqueous solution by adding the calculated amount of 4N sodium hydroxide to obtain a solution of pH 8.8. The solution is evaporated in vacuo to a small volume, diluted in ten times its volume of n-butanol and evaporated again in vacuo, thus obtaining yellow crystals which are collected, washed with water. acetone and dry under vacuum at 60 ° C to obtain the sodium salt.
Analysis:
Calculated for Cl4Hl0N304Na Na 7.49%
Found Na 7.52% CLAIM I
Process for preparing the compound of formula:
EMI1.2
characterized in that 1-vinyl-2- (4-formylstyryl) -5-nitroimidazole is oxidized and the resulting acid is isolated as such or as a salt.
SUB-CLAIMS
1. Method according to claim I, characterized in that the oxidation is carried out by means of chromic acid.
2. Method according to claim I or sub-claim 1, characterized in that the acid is isolated in the form of its sodium salt.
4. Method according to claim I or sub-claim 1, characterized in that the acid obtained is converted into an ester.
CLAIM II
Use of the acid obtained according to the process according to Claim I for the preparation of an amide of this acid.
** ATTENTION ** end of DESC field can contain start of CLMS **.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH763472A CH550179A (en) | 1969-08-25 | 1969-08-25 | 2-substituted vinyl-5-nitroimidazoles active against - trypanosoma-amdebae and trichomonas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH763472A CH550179A (en) | 1969-08-25 | 1969-08-25 | 2-substituted vinyl-5-nitroimidazoles active against - trypanosoma-amdebae and trichomonas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH550179A true CH550179A (en) | 1974-06-14 |
Family
ID=4328177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH763472A CH550179A (en) | 1969-08-25 | 1969-08-25 | 2-substituted vinyl-5-nitroimidazoles active against - trypanosoma-amdebae and trichomonas |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH550179A (en) |
-
1969
- 1969-08-25 CH CH763472A patent/CH550179A/en not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |