CH650249A5 - Basische oximaether, solche enthaltende pharmazeutische praeparate und verfahren zur herstellung derselben. - Google Patents
Basische oximaether, solche enthaltende pharmazeutische praeparate und verfahren zur herstellung derselben. Download PDFInfo
- Publication number
- CH650249A5 CH650249A5 CH5103/80A CH510380A CH650249A5 CH 650249 A5 CH650249 A5 CH 650249A5 CH 5103/80 A CH5103/80 A CH 5103/80A CH 510380 A CH510380 A CH 510380A CH 650249 A5 CH650249 A5 CH 650249A5
- Authority
- CH
- Switzerland
- Prior art keywords
- piperazinyl
- cyclohexane
- methyl
- propoxyimino
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 42
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 claims description 41
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 33
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 26
- -1 ethylene, propylene Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 12
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 12
- 239000012312 sodium hydride Substances 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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- 125000005843 halogen group Chemical group 0.000 claims description 2
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- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000576 food coloring agent Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 208000022084 motor paralysis Diseases 0.000 description 1
- QOWGVPWARWFAJW-UHFFFAOYSA-N n-(2-butylidenecycloheptylidene)hydroxylamine Chemical compound CCCC=C1CCCCCC1=NO QOWGVPWARWFAJW-UHFFFAOYSA-N 0.000 description 1
- NYZSNIIBDUFSHW-UHFFFAOYSA-N n-(2-hexylidenecyclohexylidene)hydroxylamine Chemical compound CCCCCC=C1CCCCC1=NO NYZSNIIBDUFSHW-UHFFFAOYSA-N 0.000 description 1
- UCSDIYVPGVRMTL-UHFFFAOYSA-N n-(2-octylidenecyclohexylidene)hydroxylamine Chemical compound CCCCCCCC=C1CCCCC1=NO UCSDIYVPGVRMTL-UHFFFAOYSA-N 0.000 description 1
- AEEVMRARHUYOTB-UHFFFAOYSA-N n-(2-pentylidenecyclohexylidene)hydroxylamine Chemical compound CCCCC=C1CCCCC1=NO AEEVMRARHUYOTB-UHFFFAOYSA-N 0.000 description 1
- SHNZQPAVTYGGOY-UHFFFAOYSA-N n-(2-propylidenecyclohexylidene)hydroxylamine Chemical compound CCC=C1CCCCC1=NO SHNZQPAVTYGGOY-UHFFFAOYSA-N 0.000 description 1
- IRHJAGVVWRHCSS-UHFFFAOYSA-N n-[3-(4-methylpiperazin-1-yl)propoxy]-2-propylidenecyclohexan-1-imine Chemical compound CCC=C1CCCCC1=NOCCCN1CCN(C)CC1 IRHJAGVVWRHCSS-UHFFFAOYSA-N 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
- JGLYFEDZRXNSGB-UHFFFAOYSA-N o-[2-(diethylamino)ethyl]hydroxylamine;dihydrochloride Chemical compound Cl.Cl.CCN(CC)CCON JGLYFEDZRXNSGB-UHFFFAOYSA-N 0.000 description 1
- UBVSMBHQHHGRSR-UHFFFAOYSA-N o-[2-(dimethylamino)ethyl]hydroxylamine;dihydrochloride Chemical compound Cl.Cl.CN(C)CCON UBVSMBHQHHGRSR-UHFFFAOYSA-N 0.000 description 1
- PYFGJQMBSIBLKX-UHFFFAOYSA-N o-[3-(4-methylpiperazin-1-yl)propyl]hydroxylamine;trihydrochloride Chemical compound Cl.Cl.Cl.CN1CCN(CCCON)CC1 PYFGJQMBSIBLKX-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 210000003497 sciatic nerve Anatomy 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QDWJJTJNXAKQKD-UHFFFAOYSA-N trihexyphenidyl hydrochloride Chemical compound Cl.C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 QDWJJTJNXAKQKD-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79EE2675A HU180739B (en) | 1979-07-03 | 1979-07-03 | Process for producing basic oxime-ethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH650249A5 true CH650249A5 (de) | 1985-07-15 |
Family
ID=10995855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5103/80A CH650249A5 (de) | 1979-07-03 | 1980-07-02 | Basische oximaether, solche enthaltende pharmazeutische praeparate und verfahren zur herstellung derselben. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4395413A (en, 2012) |
| JP (1) | JPS5610161A (en, 2012) |
| AT (1) | AT372677B (en, 2012) |
| AU (1) | AU530184B2 (en, 2012) |
| BE (1) | BE884083A (en, 2012) |
| CA (1) | CA1146170A (en, 2012) |
| CH (1) | CH650249A5 (en, 2012) |
| CS (1) | CS217979B2 (en, 2012) |
| DD (1) | DD151933A5 (en, 2012) |
| DE (1) | DE3025238A1 (en, 2012) |
| DK (1) | DK150197C (en, 2012) |
| ES (1) | ES8105704A1 (en, 2012) |
| FI (1) | FI70579C (en, 2012) |
| FR (1) | FR2460294A1 (en, 2012) |
| GB (1) | GB2055808B (en, 2012) |
| GR (1) | GR68751B (en, 2012) |
| HU (1) | HU180739B (en, 2012) |
| IL (1) | IL60359A (en, 2012) |
| IT (1) | IT1148881B (en, 2012) |
| NL (1) | NL190371C (en, 2012) |
| NO (1) | NO148451C (en, 2012) |
| PL (1) | PL122750B1 (en, 2012) |
| SE (1) | SE446979B (en, 2012) |
| SU (1) | SU927111A3 (en, 2012) |
| YU (2) | YU42672B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU188250B (en) * | 1983-02-08 | 1986-03-28 | Egyt Gyogyszervegyeszeti Gyar,Hu | Process for producing of basical oxim-ethers |
| HU189227B (en) * | 1983-02-08 | 1986-06-30 | Egyt Gyogyszervegyeszeti Gyar,Hu | Process for preparing basic oxime-ethers |
| US4735943A (en) * | 1984-06-29 | 1988-04-05 | Sanwa Kagaku Kenkyusho Co., Ltd. | Eburnamonine oxime derivatives, salts thereof, and pharmaceutical agents containing the same |
| HU197205B (en) * | 1984-07-10 | 1989-03-28 | Egyt Gyogyszervegyeszeti Gyar | Process for production of medical compositions against angine |
| FR2593501B1 (fr) * | 1986-01-29 | 1988-05-06 | Panmedica Sa | Nouveaux derives bis (r-oxyimino)-5,7 dihydro-6,7 (5h) dibenzo (a,c) cycloheptene, leurs procedes de preparation et leur application comme medicaments |
| HU202195B (en) * | 1987-12-31 | 1991-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing new substituted styrene derivatives and medical compositions comprising such compounds |
| HUT67314A (en) * | 1993-04-09 | 1995-03-28 | Egyt Gyogyszervegyeszeti Gyar | Process for prepg. new trisubstituted cykloalkane deriv.s and pharmaceutical compn.s contg. them |
| FR2728571B1 (fr) * | 1994-12-22 | 1997-01-31 | Adir | Nouveaux ethers d'oximes tricycliques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| DE19722848A1 (de) * | 1997-05-23 | 1998-11-26 | Schering Ag | Leukotrien-B¶4¶-Derivate, insbesondere Oximo-LTB¶4¶-Antagonisten |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1733462A (en) * | 1926-09-23 | 1929-10-29 | Winthrop Chem Co Inc | New basic oxime ethers of cyclic compounds |
| GB1493222A (en) * | 1976-01-27 | 1977-11-30 | Egyt Gyogyszervegyeszeti Gyar | Cycloalkanone oxime ethers and process for the preparation thereof |
| US4083978A (en) * | 1976-01-27 | 1978-04-11 | Egyt Gyogyszervegyeszeti Gyar | Oxime ethers |
-
1979
- 1979-07-03 HU HU79EE2675A patent/HU180739B/hu not_active IP Right Cessation
-
1980
- 1980-06-19 IL IL60359A patent/IL60359A/xx not_active IP Right Cessation
- 1980-06-24 US US06/162,674 patent/US4395413A/en not_active Expired - Lifetime
- 1980-06-26 GB GB8020989A patent/GB2055808B/en not_active Expired
- 1980-06-27 FR FR8014305A patent/FR2460294A1/fr active Granted
- 1980-06-30 BE BE1/9871A patent/BE884083A/fr not_active IP Right Cessation
- 1980-06-30 ES ES492949A patent/ES8105704A1/es not_active Expired
- 1980-07-01 GR GR62323A patent/GR68751B/el unknown
- 1980-07-01 SE SE8004868A patent/SE446979B/sv not_active IP Right Cessation
- 1980-07-01 FI FI802111A patent/FI70579C/fi not_active IP Right Cessation
- 1980-07-02 CH CH5103/80A patent/CH650249A5/de not_active IP Right Cessation
- 1980-07-02 SU SU802942954A patent/SU927111A3/ru active
- 1980-07-02 DK DK286480A patent/DK150197C/da not_active IP Right Cessation
- 1980-07-02 AU AU60035/80A patent/AU530184B2/en not_active Ceased
- 1980-07-02 PL PL1980225405A patent/PL122750B1/pl unknown
- 1980-07-02 AT AT0344880A patent/AT372677B/de not_active IP Right Cessation
- 1980-07-02 JP JP8926880A patent/JPS5610161A/ja active Granted
- 1980-07-02 NO NO801993A patent/NO148451C/no unknown
- 1980-07-03 NL NLAANVRAGE8003846,A patent/NL190371C/xx not_active IP Right Cessation
- 1980-07-03 IT IT23208/80A patent/IT1148881B/it active
- 1980-07-03 CA CA000355280A patent/CA1146170A/en not_active Expired
- 1980-07-03 YU YU1742/80A patent/YU42672B/xx unknown
- 1980-07-03 CS CS804775A patent/CS217979B2/cs unknown
- 1980-07-03 DD DD80222378A patent/DD151933A5/de not_active IP Right Cessation
- 1980-07-03 DE DE19803025238 patent/DE3025238A1/de active Granted
-
1984
- 1984-02-27 YU YU359/84A patent/YU43344B/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |