GB1587258A - Production of substituted guanidines - Google Patents
Production of substituted guanidines Download PDFInfo
- Publication number
- GB1587258A GB1587258A GB2553377A GB2553377A GB1587258A GB 1587258 A GB1587258 A GB 1587258A GB 2553377 A GB2553377 A GB 2553377A GB 2553377 A GB2553377 A GB 2553377A GB 1587258 A GB1587258 A GB 1587258A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiourea
- salt
- substituted
- formula
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002357 guanidines Chemical class 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 15
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 15
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 9
- 230000008018 melting Effects 0.000 claims description 9
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 235000009518 sodium iodide Nutrition 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CRMWDHWPEFVLOU-UHFFFAOYSA-N n,n'-dimethylmethanimidamide Chemical compound CNC=NC CRMWDHWPEFVLOU-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- GKVUQZXKYCDPBJ-UHFFFAOYSA-N N-benzyl-N'-methylmethanimidamide Chemical compound C(C1=CC=CC=C1)NC=NC GKVUQZXKYCDPBJ-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HWZWLMPFFGWOIJ-UHFFFAOYSA-N 1,2,3-trimethylguanidine;hydroiodide Chemical compound I.CNC(NC)=NC HWZWLMPFFGWOIJ-UHFFFAOYSA-N 0.000 description 1
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- APXOHENTPZBQEO-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-2,3-dimethylguanidine;hydroiodide Chemical compound I.CNC(=NC)NCC1=CC=CC=C1Cl APXOHENTPZBQEO-UHFFFAOYSA-N 0.000 description 1
- OLUXTYJVZZRQAL-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-2,3-dimethylguanidine hydroiodide Chemical compound I.CN\C(NCc1ccc(OC)cc1)=N/C OLUXTYJVZZRQAL-UHFFFAOYSA-N 0.000 description 1
- IBRUMPJVDPHEFZ-UHFFFAOYSA-N 1-benzyl-2,3-dimethylguanidine;hydroiodide Chemical compound I.CNC(=NC)NCC1=CC=CC=C1 IBRUMPJVDPHEFZ-UHFFFAOYSA-N 0.000 description 1
- GDUBTTXVKWIAKV-UHFFFAOYSA-N 1-benzyl-3-methylthiourea Chemical compound CNC(=S)NCC1=CC=CC=C1 GDUBTTXVKWIAKV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- -1 S-substituted isothiourea Chemical class 0.000 description 1
- FRAKPEDRQISJEU-UHFFFAOYSA-N [I-].C[N+](=C(N)N)C Chemical compound [I-].C[N+](=C(N)N)C FRAKPEDRQISJEU-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- RMUKCGUDVKEQPL-UHFFFAOYSA-K triiodoindigane Chemical compound I[In](I)I RMUKCGUDVKEQPL-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2553377A GB1587258A (en) | 1977-06-17 | 1977-06-17 | Production of substituted guanidines |
| NZ18755778A NZ187557A (en) | 1977-06-17 | 1978-06-13 | Preparation of guanidine derivatives |
| DK265978A DK158977C (da) | 1977-06-17 | 1978-06-14 | Fremgangsmaade til fremstilling af substituerede guanidiner eller salte deraf |
| AU37154/78A AU520839B2 (en) | 1977-06-17 | 1978-06-15 | Substituted guanidine froma thio-urea |
| JP7157778A JPS5448714A (en) | 1977-06-17 | 1978-06-15 | Manufacture of guanidines having substituent |
| DE19782826452 DE2826452C2 (de) | 1977-06-17 | 1978-06-16 | Verfahren zur Herstellung von substituierten Guanidinen |
| CA305,594A CA1083603A (en) | 1977-06-17 | 1978-06-16 | Production of substituted guanidines. |
| NL7806526A NL187856C (nl) | 1977-06-17 | 1978-06-16 | Werkwijze ter bereiding van gesubstitueerde guanidinen. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2553377A GB1587258A (en) | 1977-06-17 | 1977-06-17 | Production of substituted guanidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1587258A true GB1587258A (en) | 1981-04-01 |
Family
ID=10229222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2553377A Expired GB1587258A (en) | 1977-06-17 | 1977-06-17 | Production of substituted guanidines |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5448714A (da) |
| AU (1) | AU520839B2 (da) |
| CA (1) | CA1083603A (da) |
| DE (1) | DE2826452C2 (da) |
| DK (1) | DK158977C (da) |
| GB (1) | GB1587258A (da) |
| NL (1) | NL187856C (da) |
| NZ (1) | NZ187557A (da) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0195620A2 (en) * | 1985-03-15 | 1986-09-24 | McNeilab, Inc. | Process for producing guanidines such as linogliride and process for intermediates |
| US4656291A (en) * | 1985-03-15 | 1987-04-07 | Mcneilab, Inc. | Process for producing amidine sulfonic acids |
| US4693850A (en) * | 1985-03-15 | 1987-09-15 | Mcneilab, Inc. | Methane sulfonic acid derivatives |
| EP0260118A1 (en) * | 1986-09-10 | 1988-03-16 | Syntex (U.S.A.) Inc. | Selective amidination of diamines |
| US4781866A (en) * | 1985-03-15 | 1988-11-01 | Mcneilab, Inc. | Process for producing amidine sulfonic acid intermediates for guanidines |
| EP0299533A3 (en) * | 1987-07-17 | 1989-07-19 | The Nutrasweet Company | High potency sweetening agents |
| US4851094A (en) * | 1985-03-15 | 1989-07-25 | Mcneilab, Inc. | Process for producing amidine sulfonic acid intermediates for guanidines |
| EP0351350A1 (en) * | 1988-07-12 | 1990-01-17 | THE NUTRASWEET COMPANY (a Delaware corporation) | High potency sweetening agents |
| US5840972A (en) * | 1993-05-06 | 1998-11-24 | Glaxo Wellcome Inc. | Process for preparing NG -monoalkyl-L-arginine and related compounds |
| US5948939A (en) * | 1986-09-10 | 1999-09-07 | Syntex (U.S.A.) Inc. | Selective amidination of diamines |
| CN102363602A (zh) * | 2011-09-20 | 2012-02-29 | 科迈化工股份有限公司 | 以双氧水为氧化剂生产硫化促进剂dpg的方法 |
| CN102363601A (zh) * | 2011-09-20 | 2012-02-29 | 科迈化工股份有限公司 | 以双氧水为氧化剂生产橡胶促进剂dgp的方法 |
| CN110407720A (zh) * | 2019-08-20 | 2019-11-05 | 西安近代化学研究所 | 一种碘催化硫脲脱硫制备取代胍的合成方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6043414U (ja) * | 1983-08-29 | 1985-03-27 | 本田技研工業株式会社 | 自動二輪車等のヒ−タ装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB973882A (en) * | 1959-12-23 | 1964-10-28 | Wellcome Found | Benzyl-guanidines,their preparation and pharmaceutical compositions containing them |
-
1977
- 1977-06-17 GB GB2553377A patent/GB1587258A/en not_active Expired
-
1978
- 1978-06-13 NZ NZ18755778A patent/NZ187557A/xx unknown
- 1978-06-14 DK DK265978A patent/DK158977C/da active
- 1978-06-15 JP JP7157778A patent/JPS5448714A/ja active Granted
- 1978-06-15 AU AU37154/78A patent/AU520839B2/en not_active Expired
- 1978-06-16 CA CA305,594A patent/CA1083603A/en not_active Expired
- 1978-06-16 NL NL7806526A patent/NL187856C/xx not_active IP Right Cessation
- 1978-06-16 DE DE19782826452 patent/DE2826452C2/de not_active Expired
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4851094A (en) * | 1985-03-15 | 1989-07-25 | Mcneilab, Inc. | Process for producing amidine sulfonic acid intermediates for guanidines |
| US4781866A (en) * | 1985-03-15 | 1988-11-01 | Mcneilab, Inc. | Process for producing amidine sulfonic acid intermediates for guanidines |
| US4656270A (en) * | 1985-03-15 | 1987-04-07 | Mcneilab, Inc. | Process for producing guanidines such as linogliride |
| EP0195620A3 (en) * | 1985-03-15 | 1987-08-19 | McNeilab, Inc. | Process for producing guanidines such as linogliride and process for intermediates |
| EP0195620A2 (en) * | 1985-03-15 | 1986-09-24 | McNeilab, Inc. | Process for producing guanidines such as linogliride and process for intermediates |
| US4693850A (en) * | 1985-03-15 | 1987-09-15 | Mcneilab, Inc. | Methane sulfonic acid derivatives |
| US4656291A (en) * | 1985-03-15 | 1987-04-07 | Mcneilab, Inc. | Process for producing amidine sulfonic acids |
| EP0260118A1 (en) * | 1986-09-10 | 1988-03-16 | Syntex (U.S.A.) Inc. | Selective amidination of diamines |
| US5948939A (en) * | 1986-09-10 | 1999-09-07 | Syntex (U.S.A.) Inc. | Selective amidination of diamines |
| EP0299533A3 (en) * | 1987-07-17 | 1989-07-19 | The Nutrasweet Company | High potency sweetening agents |
| EP0351350A1 (en) * | 1988-07-12 | 1990-01-17 | THE NUTRASWEET COMPANY (a Delaware corporation) | High potency sweetening agents |
| US5840972A (en) * | 1993-05-06 | 1998-11-24 | Glaxo Wellcome Inc. | Process for preparing NG -monoalkyl-L-arginine and related compounds |
| CN102363602A (zh) * | 2011-09-20 | 2012-02-29 | 科迈化工股份有限公司 | 以双氧水为氧化剂生产硫化促进剂dpg的方法 |
| CN102363601A (zh) * | 2011-09-20 | 2012-02-29 | 科迈化工股份有限公司 | 以双氧水为氧化剂生产橡胶促进剂dgp的方法 |
| CN110407720A (zh) * | 2019-08-20 | 2019-11-05 | 西安近代化学研究所 | 一种碘催化硫脲脱硫制备取代胍的合成方法 |
| CN110407720B (zh) * | 2019-08-20 | 2021-07-27 | 西安近代化学研究所 | 一种碘催化硫脲脱硫制备取代胍的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7806526A (nl) | 1978-12-19 |
| AU520839B2 (en) | 1982-03-04 |
| DE2826452A1 (de) | 1979-01-11 |
| CA1083603A (en) | 1980-08-12 |
| NZ187557A (en) | 1980-08-26 |
| JPS5748106B2 (da) | 1982-10-14 |
| DK158977B (da) | 1990-08-13 |
| NL187856C (nl) | 1992-02-03 |
| DK158977C (da) | 1991-01-21 |
| DE2826452C2 (de) | 1987-01-22 |
| DK265978A (da) | 1978-12-18 |
| NL187856B (nl) | 1991-09-02 |
| JPS5448714A (en) | 1979-04-17 |
| AU3715478A (en) | 1979-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| EER | Erroneous entry in the register of patents: |
Free format text: DOCUMENT WAS IDENTIFIED AS HAVING CEASED WHILE IN FACT IT WAS STILL IN FORCE |
|
| EER | Erroneous entry in the register of patents: |
Free format text: DOCUMENT WAS IDENTIFIED AS HAVING CEASED WHILE IN FACT IT WAS STILL IN FORCE |
|
| EER | Erroneous entry in the register of patents: |
Free format text: DOCUMENT WAS IDENTIFIED AS HAVING CEASED WHILE IN FACT IT WAS STILL IN FORCE |
|
| EER | Erroneous entry in the register of patents: |
Free format text: DOCUMENT WAS IDENTIFIED AS HAVING CEASED WHILE IN FACT IT WAS STILL IN FORCE |
|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940530 |