GB1458029A - Sulphamylbenzoic acids and preparation thereof - Google Patents
Sulphamylbenzoic acids and preparation thereofInfo
- Publication number
- GB1458029A GB1458029A GB5720773A GB5720773A GB1458029A GB 1458029 A GB1458029 A GB 1458029A GB 5720773 A GB5720773 A GB 5720773A GB 5720773 A GB5720773 A GB 5720773A GB 1458029 A GB1458029 A GB 1458029A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- alkyl
- prepared
- hexamethyleneimino
- 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
- KDNIOKSLVIGAAN-UHFFFAOYSA-N 2-sulfamoylbenzoic acid Chemical class NS(=O)(=O)C1=CC=CC=C1C(O)=O KDNIOKSLVIGAAN-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- -1 hexamethyleneimino Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 2
- XXGZTPVQCLURSV-UHFFFAOYSA-N 2,3-dichloro-5-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC(S(Cl)(=O)=O)=CC(Cl)=C1Cl XXGZTPVQCLURSV-UHFFFAOYSA-N 0.000 abstract 1
- RVCLISIPGZGQPU-UHFFFAOYSA-N 2,6-dichloro-3-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC(S(Cl)(=O)=O)=C1Cl RVCLISIPGZGQPU-UHFFFAOYSA-N 0.000 abstract 1
- MRUDNSFOFOQZDA-UHFFFAOYSA-N 2,6-dichlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC=C1Cl MRUDNSFOFOQZDA-UHFFFAOYSA-N 0.000 abstract 1
- 201000001320 Atherosclerosis Diseases 0.000 abstract 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- VCTRCRPZMQJTFF-UHFFFAOYSA-N methyl 2-chloro-3-chlorosulfonylbenzoate Chemical compound COC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1Cl VCTRCRPZMQJTFF-UHFFFAOYSA-N 0.000 abstract 1
- JBCQPBVZKBEHNF-UHFFFAOYSA-N methyl 2-chloro-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1Cl JBCQPBVZKBEHNF-UHFFFAOYSA-N 0.000 abstract 1
- NKBQKMXNIWIFAE-UHFFFAOYSA-N methyl 3-amino-2-chlorobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1Cl NKBQKMXNIWIFAE-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 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
- C07D295/22—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 hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- 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
- C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1458029 Sulphamylbenzoic acids PFIZER Inc 10 Dec 1973 [26 Dec 1972] 57207/73 Addition to 1353357 Heading C2C Novel compounds of Formula I (in which Q is H, Cl, F, Br, 1-4C alkoxy, di- (1-4C alkyl)amino, OH, SCH 3 , piperidino or hexamethyleneimino; T is Cl, F, Br, CH 3 , OCH 3 or CF 3 ; R<SP>16</SP> is H or 2-4C alkyl; and R<SP>17</SP> is 2-4C alkyl or a group of Formula II in which n is 1-3; and R 10 and R 11 are H, Cl, Br, CH3 or phenyl; with the proviso that where R<SP>17</SP> is 2-4C alkyl, R<SP>16</SP> is not H; or -NR<SP>16</SP>R<SP>17</SP> is morpholino, piperidino, mono- or di-methylpiperidino or hexamethyleneimino) and amides, 1-4C alkyl esters and salts thereof are prepared by reacting an amine R<SP>16</SP>R<SP>17</SP>NH with a compound of Formula III (in which Hal is halo); or by hydrolysis of a compound of Formula IV or by reacting a compound of Formula V (a) with a 1-4C alkanol or CH 3 SH in the presence of a base to give a compound of Formula I in which O is 1-4C alkoxy or SCH 3 ; (b) with an amine R<SP>1</SP>R<SP>11</SP>NH to give a compound of Formula I in which Q is NR<SP>1</SP>R<SP>1</SP> and, R<SP>1</SP> and R<SP>11</SP> are 1-4C alkyl or NR<SP>1</SP>R<SP>11</SP> is piperidino or hexamethyleneimino; or (c) with a base to give a compound of Formula I in which Q is OH. 2,3 - Dichloro - 5 - chlorosulphonyl - benzoic acid is prepared by reaction of 2,6-dichlorobenzoic acid with chlorosulphonic acid. 2,6- Dichloro - 5 - chlorosulphonyl - benzoic acid is prepared in a similar manner. Methyl 3-amino- 2-chlorobenzoate HCl. is prepared by reduction of methyl 3-nitro-2-chlorobenzoate with SnCl 2 / HCl. Methyl 2 - chloro - 3 - chlorosulphonylbenzoate is prepared by reaction of the previous intermediate with NaNO 2 , then SO 2 and CuCl 2 . Pharmaceutical compositions used in treating atherosclerosis comprise a compound of Formula I together with a suitable carrier and are administered orally or parenterally.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00318213A US3843662A (en) | 1971-12-09 | 1972-12-26 | 2-halo-5-(substituted piperidino sulfonyl)benzoic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1458029A true GB1458029A (en) | 1976-12-08 |
Family
ID=23237158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5720773A Expired GB1458029A (en) | 1972-12-26 | 1973-12-10 | Sulphamylbenzoic acids and preparation thereof |
Country Status (11)
| Country | Link |
|---|---|
| JP (2) | JPS4986522A (en) |
| AR (1) | AR214849A1 (en) |
| AU (1) | AU6366973A (en) |
| BE (1) | BE808939R (en) |
| CA (1) | CA1012974A (en) |
| DE (1) | DE2363786A1 (en) |
| ES (2) | ES421767A2 (en) |
| FR (1) | FR2211261B2 (en) |
| GB (1) | GB1458029A (en) |
| NL (1) | NL7317455A (en) |
| ZA (1) | ZA739662B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0068407A1 (en) * | 1981-06-22 | 1983-01-05 | Hodogaya Chemical Co., Ltd. | Aminosulfonylbenzoic acid derivatives |
| US4999134A (en) * | 1987-09-25 | 1991-03-12 | Basf Aktiengesellschaft | Zinc salts, lead salts and/or calcium salts of carboxylic acids and their use as corrosion inhibitors |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0068408A1 (en) * | 1980-11-10 | 1983-01-05 | Mochida Pharmaceutical Co., Ltd. | Antiviral compositions and a method for treating virus diseases |
| EP0132540A1 (en) * | 1981-06-22 | 1985-02-13 | Mochida Pharmaceutical Co., Ltd. | Antiviral compositions |
| DE19941540C2 (en) * | 1999-09-01 | 2002-08-29 | Aventis Pharma Gmbh | Sulfonylcarboxamides for the manufacture of medicaments for the prophylaxis or treatment of hyperlipidemia |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1122541B (en) * | 1959-12-28 | 1962-01-25 | Hoechst Ag | Process for the production of sulfamyl-anthranilic acids |
| FR1472906A (en) * | 1961-05-08 | 1967-03-17 | Parke Davis & Co | Esters of 4-halo-3-sulfamoylbenzoic acids and their production process |
| FR1450358A (en) * | 1960-09-03 | 1966-06-24 | Parke Davis & Co | Production of new 4-halogeno-3-sulfamylbenzamides |
| FR1311859A (en) * | 1961-09-18 | 1962-12-14 | Soc Ind Fab Antibiotiques Sifa | New sulfonamide derivatives, and method of preparation |
| US3565920A (en) * | 1966-12-29 | 1971-02-23 | Ciba Geigy Corp | 5-sulfamyl-anthranilic acids |
| US3567746A (en) * | 1968-07-10 | 1971-03-02 | Pennwalt Corp | N-aryl benzamides |
| US3700773A (en) * | 1969-06-25 | 1972-10-24 | Merck & Co Inc | Substituted phenylsulfamyl salicyclic acids and derivatives thereof in the treatment of inflammation |
-
1973
- 1973-12-10 GB GB5720773A patent/GB1458029A/en not_active Expired
- 1973-12-14 AU AU63669/73A patent/AU6366973A/en not_active Expired
- 1973-12-17 CA CA188,289A patent/CA1012974A/en not_active Expired
- 1973-12-20 NL NL7317455A patent/NL7317455A/xx not_active Application Discontinuation
- 1973-12-21 DE DE2363786A patent/DE2363786A1/en active Pending
- 1973-12-21 ZA ZA00739662A patent/ZA739662B/en unknown
- 1973-12-21 BE BE1005596A patent/BE808939R/en active
- 1973-12-24 ES ES421767A patent/ES421767A2/en not_active Expired
- 1973-12-26 JP JP48144187A patent/JPS4986522A/ja active Pending
- 1973-12-26 AR AR251706A patent/AR214849A1/en active
- 1973-12-26 FR FR7346294A patent/FR2211261B2/fr not_active Expired
-
1974
- 1974-04-10 ES ES74425208A patent/ES425208A1/en not_active Expired
-
1981
- 1981-12-01 JP JP56193584A patent/JPS5924975B2/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0068407A1 (en) * | 1981-06-22 | 1983-01-05 | Hodogaya Chemical Co., Ltd. | Aminosulfonylbenzoic acid derivatives |
| US4999134A (en) * | 1987-09-25 | 1991-03-12 | Basf Aktiengesellschaft | Zinc salts, lead salts and/or calcium salts of carboxylic acids and their use as corrosion inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| ES421767A2 (en) | 1977-07-01 |
| CA1012974A (en) | 1977-06-28 |
| FR2211261A2 (en) | 1974-07-19 |
| FR2211261B2 (en) | 1977-04-15 |
| BE808939R (en) | 1974-06-21 |
| AU6366973A (en) | 1975-06-19 |
| JPS4986522A (en) | 1974-08-19 |
| ES425208A1 (en) | 1976-06-16 |
| AR214849A1 (en) | 1979-08-15 |
| NL7317455A (en) | 1974-06-28 |
| JPS5924975B2 (en) | 1984-06-13 |
| JPS58170756A (en) | 1983-10-07 |
| DE2363786A1 (en) | 1974-07-11 |
| ZA739662B (en) | 1975-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |