NL8100695A - Rifamycineverbindingen. - Google Patents
Rifamycineverbindingen. Download PDFInfo
- Publication number
- NL8100695A NL8100695A NL8100695A NL8100695A NL8100695A NL 8100695 A NL8100695 A NL 8100695A NL 8100695 A NL8100695 A NL 8100695A NL 8100695 A NL8100695 A NL 8100695A NL 8100695 A NL8100695 A NL 8100695A
- Authority
- NL
- Netherlands
- Prior art keywords
- compounds
- general formula
- solution
- rifamycin
- added
- Prior art date
Links
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical class OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 title claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229940109171 rifamycin sv Drugs 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 2
- HJYYPODYNSCCOU-ZDHWWVNNSA-N Rifamycin SV Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(O)c4c3C2=O HJYYPODYNSCCOU-ZDHWWVNNSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- -1 ethyl dimethylformiminium chloride Chemical compound 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229960003292 rifamycin Drugs 0.000 description 2
- NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 description 1
- 229930195573 Amycin Natural products 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241001522878 Escherichia coli B Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- TZWVZSVXLWFKKI-UHFFFAOYSA-N fluoroform methanol Chemical compound CO.C(F)(F)F TZWVZSVXLWFKKI-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8004848 | 1980-02-13 | ||
| GB8004848 | 1980-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8100695A true NL8100695A (nl) | 1981-09-16 |
Family
ID=10511321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8100695A NL8100695A (nl) | 1980-02-13 | 1981-02-12 | Rifamycineverbindingen. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4305941A (en, 2012) |
| JP (1) | JPS56128785A (en, 2012) |
| AT (1) | AT373891B (en, 2012) |
| AU (1) | AU533176B2 (en, 2012) |
| BE (1) | BE886395A (en, 2012) |
| CA (1) | CA1173030A (en, 2012) |
| CH (1) | CH649770A5 (en, 2012) |
| DE (1) | DE3100612A1 (en, 2012) |
| DK (1) | DK11381A (en, 2012) |
| ES (1) | ES8202030A1 (en, 2012) |
| FI (1) | FI69079C (en, 2012) |
| FR (1) | FR2475552A1 (en, 2012) |
| GR (1) | GR71862B (en, 2012) |
| IE (1) | IE51144B1 (en, 2012) |
| IL (1) | IL61861A (en, 2012) |
| IT (1) | IT1136558B (en, 2012) |
| NL (1) | NL8100695A (en, 2012) |
| NZ (1) | NZ195943A (en, 2012) |
| PT (1) | PT72499B (en, 2012) |
| SE (1) | SE453194B (en, 2012) |
| SU (1) | SU1047391A3 (en, 2012) |
| YU (1) | YU31781A (en, 2012) |
| ZA (1) | ZA8140B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8308166D0 (en) * | 1983-03-24 | 1983-05-05 | Erba Farmitalia | Preparation of azinomethyl-rifamycins |
| IT1201963B (it) * | 1983-03-24 | 1989-02-02 | Prodotti Antibiotici Spa | Derivati delle rifamicine e procedimento per la loro preparazione |
| US7122525B2 (en) * | 2001-11-21 | 2006-10-17 | Activbiotics, Inc. | Targeted therapeutics and uses thereof |
| US7820652B2 (en) * | 2003-09-24 | 2010-10-26 | Activbiotics Pharma, Llc | Regimen for the administration of rifamycin-class antibiotics |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1048565B (it) * | 1975-05-15 | 1980-12-20 | Archifar Ind Chim Trentino | Amine aromatiche |
| IT1056271B (it) * | 1975-05-20 | 1982-01-30 | Archifar Ind Chim Trentino | Prodotti derivati dalle amine aromatiche |
| IT1056272B (it) * | 1975-06-13 | 1982-01-30 | Archifar Ind Chim Trentino | Prodotti derivati dalle amine aromatiche |
| DK345977A (da) * | 1976-09-30 | 1978-03-31 | Archifar Ind Chim Trentino | G rifamycinforbindelser og fremgangsmaade til deres fremstillin |
-
1980
- 1980-11-28 BE BE0/202966A patent/BE886395A/fr not_active IP Right Cessation
-
1981
- 1981-01-05 IE IE4/81A patent/IE51144B1/en unknown
- 1981-01-05 ZA ZA00810040A patent/ZA8140B/xx unknown
- 1981-01-05 US US06/222,618 patent/US4305941A/en not_active Expired - Fee Related
- 1981-01-06 IL IL61861A patent/IL61861A/xx unknown
- 1981-01-06 NZ NZ195943A patent/NZ195943A/xx unknown
- 1981-01-08 FI FI810038A patent/FI69079C/fi not_active IP Right Cessation
- 1981-01-08 GR GR63818A patent/GR71862B/el unknown
- 1981-01-12 DE DE19813100612 patent/DE3100612A1/de not_active Ceased
- 1981-01-12 DK DK11381A patent/DK11381A/da not_active Application Discontinuation
- 1981-01-14 CH CH207/81A patent/CH649770A5/it not_active IP Right Cessation
- 1981-01-19 IT IT19187/81A patent/IT1136558B/it active
- 1981-01-23 FR FR8101219A patent/FR2475552A1/fr active Granted
- 1981-01-23 AT AT0028181A patent/AT373891B/de not_active IP Right Cessation
- 1981-01-23 SU SU813232526A patent/SU1047391A3/ru active
- 1981-01-30 SE SE8100743A patent/SE453194B/sv not_active IP Right Cessation
- 1981-02-05 CA CA000370178A patent/CA1173030A/en not_active Expired
- 1981-02-06 YU YU00317/81A patent/YU31781A/xx unknown
- 1981-02-12 AU AU67253/81A patent/AU533176B2/en not_active Ceased
- 1981-02-12 ES ES499356A patent/ES8202030A1/es not_active Expired
- 1981-02-12 PT PT72499A patent/PT72499B/pt unknown
- 1981-02-12 NL NL8100695A patent/NL8100695A/nl not_active Application Discontinuation
- 1981-02-13 JP JP1913381A patent/JPS56128785A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1173030A (en) | 1984-08-21 |
| IE51144B1 (en) | 1986-10-15 |
| DK11381A (da) | 1981-08-14 |
| ES499356A0 (es) | 1982-01-16 |
| NZ195943A (en) | 1982-12-07 |
| IL61861A (en) | 1984-03-30 |
| BE886395A (fr) | 1981-03-16 |
| SU1047391A3 (ru) | 1983-10-07 |
| YU31781A (en) | 1983-09-30 |
| IL61861A0 (en) | 1981-02-27 |
| IT1136558B (it) | 1986-09-03 |
| US4305941A (en) | 1981-12-15 |
| FI810038L (fi) | 1981-08-14 |
| AU6725381A (en) | 1981-08-20 |
| FI69079B (fi) | 1985-08-30 |
| SE453194B (sv) | 1988-01-18 |
| ATA28181A (de) | 1983-07-15 |
| JPS6155918B2 (en, 2012) | 1986-11-29 |
| DE3100612A1 (de) | 1981-12-03 |
| AT373891B (de) | 1984-02-27 |
| PT72499A (en) | 1981-03-01 |
| PT72499B (en) | 1982-02-05 |
| ZA8140B (en) | 1982-01-27 |
| FI69079C (fi) | 1985-12-10 |
| FR2475552A1 (fr) | 1981-08-14 |
| FR2475552B1 (en, 2012) | 1985-02-15 |
| IE810004L (en) | 1981-08-13 |
| JPS56128785A (en) | 1981-10-08 |
| GR71862B (en, 2012) | 1983-07-06 |
| SE8100743L (sv) | 1981-08-14 |
| AU533176B2 (en) | 1983-11-03 |
| CH649770A5 (it) | 1985-06-14 |
| IT8119187A0 (it) | 1981-01-19 |
| ES8202030A1 (es) | 1982-01-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI69467C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pyrido- och isokinolin(1',2':1,2)imidazo(5,4-c)rifamycin soch sv-derivat | |
| EP0533264B1 (en) | Process for the preparation of omeprazole | |
| US3780034A (en) | Process for preparing substituted cephalosporins | |
| NL8100695A (nl) | Rifamycineverbindingen. | |
| ITMI981776A1 (it) | Derivati di eritromicina ad attivita' antibiotica | |
| US4327096A (en) | 3-Amidino ansamycins | |
| US4585589A (en) | Water-soluble alkanoyloxy and alkoxycarbonyloxy rifampicin derivatives, process for its preparation, intermediates, and its pharmaceutical composition as antibacterials | |
| US4188321A (en) | 25-Desacetyl rifamycins | |
| KR860004076A (ko) | 항생 물질 l17046 에스테르 유도체의 제조방법 | |
| IE54153B1 (en) | Azino methyl-rifamycins | |
| US3625960A (en) | Rifamycin sv derivatives | |
| US3515726A (en) | 2,2'-bis(pyridyl-n-oxide) dithiolcarbonates and trithiocarbonates | |
| AU726586B2 (en) | Novel phenanthridinium derivatives | |
| FI62098C (fi) | Foerfarande foer framstaellning av tiazolo(5,4-c)rifamycin sv och dess derivat | |
| DE2445670A1 (de) | 7-(cyanomethylaryl)-acetamidocephalosporin-derivate, deren pharmazeutisch vertraegliche salze und verfahren zu deren herstellung | |
| Koster et al. | Chlorination of the cephem dihydrothiazine ring. Factors influencing C-2 substitution vs. degradation to isothiazoles1 | |
| US3625961A (en) | Rifamycins | |
| FI83877C (fi) | Foerfarande foer framstaellning av en ny terapeutiskt anvaendbar 7-(3-klorisoxazol-5-yl)-acetamido-3- (1-metyl-1h-1,2,3,4-tetrazol-5-yl)-tiometyl-cef-3-em-4-karboxylsyra | |
| CA1175807A (en) | 2.beta.-CHLOROMETHYL-2.alpha.-METHYLPENAM-3.alpha.-CARBOXYLIC ACID SULFONE | |
| DE2453601A1 (de) | Verfahren zur herstellung von 2-(substituierten thio)-2-cephemderivaten | |
| Kim et al. | Synthesis and antibacterial activity of 2-[(methoxycarbonyl) methylene] cephalosporins | |
| US3878198A (en) | {62 -Ketoacyl derivatives of 6-aminopenicillanic acid and process thereof | |
| US4183850A (en) | Process for preparing 2-acyloxymethylpenams and 3-acyloxycephams | |
| Leysen et al. | Thiazolopyridine analogs of naldixic acid. 1. Thiazolo [5, 4‐b] pyridines | |
| Naruto et al. | PHOTOLYSIS OF 4-OXO-4H-BENZISOXAZOLO [2, 3-a] PYRIDINES |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed | ||
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |