CN1060653A - 白细胞三烯拮抗药的旋光异构体的结晶方法 - Google Patents
白细胞三烯拮抗药的旋光异构体的结晶方法 Download PDFInfo
- Publication number
- CN1060653A CN1060653A CN91108031A CN91108031A CN1060653A CN 1060653 A CN1060653 A CN 1060653A CN 91108031 A CN91108031 A CN 91108031A CN 91108031 A CN91108031 A CN 91108031A CN 1060653 A CN1060653 A CN 1060653A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- isomer
- formula
- salt
- sulfo
- 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.)
- Pending
Links
- 239000003199 leukotriene receptor blocking agent Substances 0.000 title abstract description 6
- 238000002425 crystallisation Methods 0.000 title description 4
- -1 amine salt Chemical class 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 27
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 12
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- YVSFLVNWJIEJRV-UHFFFAOYSA-N 1-undecyne Chemical compound CCCCCCCCCC#C YVSFLVNWJIEJRV-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- ZVDBUOGYYYNMQI-UHFFFAOYSA-N dodec-1-yne Chemical compound CCCCCCCCCCC#C ZVDBUOGYYYNMQI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001261 hydroxy acids Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002240 furans Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 230000008014 freezing Effects 0.000 abstract description 2
- 238000007710 freezing Methods 0.000 abstract description 2
- 150000001412 amines Chemical group 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 206010062282 Silver-Russell syndrome Diseases 0.000 description 6
- 201000001845 syndromic X-linked intellectual disability Snyder type Diseases 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000004296 chiral HPLC Methods 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241001227713 Chiron Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 238000006217 Nerdel homologation reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000003912 basophilic leucocyte Anatomy 0.000 description 1
- YBKSICKROBHIFB-UHFFFAOYSA-N benzene sulfane Chemical compound C1=CC=CC=C1.S.S YBKSICKROBHIFB-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000032696 parturition Effects 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58612490A | 1990-09-21 | 1990-09-21 | |
| US586,124 | 1990-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1060653A true CN1060653A (zh) | 1992-04-29 |
Family
ID=24344408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN91108031A Pending CN1060653A (zh) | 1990-09-21 | 1991-09-21 | 白细胞三烯拮抗药的旋光异构体的结晶方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5288900A (enExample) |
| EP (1) | EP0552254A1 (enExample) |
| JP (1) | JPH06501269A (enExample) |
| KR (1) | KR930702284A (enExample) |
| CN (1) | CN1060653A (enExample) |
| AU (1) | AU662299B2 (enExample) |
| CA (1) | CA2091245A1 (enExample) |
| CZ (1) | CZ45193A3 (enExample) |
| IE (1) | IE913308A1 (enExample) |
| IL (1) | IL99578A0 (enExample) |
| MX (1) | MX9101206A (enExample) |
| MY (1) | MY131049A (enExample) |
| NZ (1) | NZ239875A (enExample) |
| PL (1) | PL296247A1 (enExample) |
| PT (1) | PT99021A (enExample) |
| SK (1) | SK21993A3 (enExample) |
| TW (1) | TW221805B (enExample) |
| WO (1) | WO1992005151A1 (enExample) |
| YU (1) | YU157091A (enExample) |
| ZA (1) | ZA917560B (enExample) |
| ZW (1) | ZW13191A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10336185A1 (de) * | 2003-08-07 | 2005-02-24 | Bayer Chemicals Ag | Enantiomerenangereicherte 1-Phenylethylamine |
| EA012114B1 (ru) * | 2005-01-24 | 2009-08-28 | Синвеншен Аг | Способ получения металлсодержащего композиционного материала и полученный материал |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4937253A (en) * | 1985-04-19 | 1990-06-26 | Smithkline Beecham Corporation | Ester prodrugs |
| US4874792A (en) * | 1985-04-19 | 1989-10-17 | Smithkline Beckman Corporation | Thiophenyl Alkanoic acids useful as leukotriene antagonists |
| US4845272A (en) * | 1987-07-10 | 1989-07-04 | Kuraray Co., Ltd. | Process for the optical resolution of (±)-cis or (±)-trans-permethric acid |
| AU610528B2 (en) * | 1987-10-29 | 1991-05-23 | Smithkline Beckman Corporation | Leukotriene antagonists |
| IT1217988B (it) * | 1988-01-28 | 1990-03-30 | Ind Chimica Profarmaco Spa | Procedimento per la risoluzione ottica di un pacemo |
| US4904822A (en) * | 1988-02-19 | 1990-02-27 | Kuraray Co., Ltd. | Process for the optical resolution of (+)-2-hydroxy-4-phenylbutanoic acid |
| IT1226300B (it) * | 1988-07-26 | 1990-12-27 | Zambon Spa | Processo per la preparazione di intermedi per la sintesi del diltiazem. |
| EP0365189B1 (en) * | 1988-10-21 | 1995-06-14 | Kabushiki Kaisha Kosmek | Quick-acting coupling |
-
1991
- 1991-09-20 MX MX9101206A patent/MX9101206A/es not_active IP Right Cessation
- 1991-09-20 PL PL29624791A patent/PL296247A1/xx unknown
- 1991-09-20 US US08/030,076 patent/US5288900A/en not_active Expired - Fee Related
- 1991-09-20 EP EP91918951A patent/EP0552254A1/en not_active Withdrawn
- 1991-09-20 IE IE330891A patent/IE913308A1/en unknown
- 1991-09-20 PT PT99021A patent/PT99021A/pt not_active Application Discontinuation
- 1991-09-20 NZ NZ239875A patent/NZ239875A/en unknown
- 1991-09-20 ZW ZW131/91A patent/ZW13191A1/xx unknown
- 1991-09-20 AU AU87675/91A patent/AU662299B2/en not_active Ceased
- 1991-09-20 CA CA002091245A patent/CA2091245A1/en not_active Abandoned
- 1991-09-20 JP JP3517260A patent/JPH06501269A/ja active Pending
- 1991-09-20 CZ CS93451A patent/CZ45193A3/cs unknown
- 1991-09-20 WO PCT/US1991/006862 patent/WO1992005151A1/en not_active Ceased
- 1991-09-20 SK SK21993A patent/SK21993A3/sk unknown
- 1991-09-21 MY MYPI91001722A patent/MY131049A/en unknown
- 1991-09-21 CN CN91108031A patent/CN1060653A/zh active Pending
- 1991-09-23 ZA ZA917560A patent/ZA917560B/xx unknown
- 1991-09-23 YU YU157091A patent/YU157091A/sh unknown
- 1991-09-26 IL IL99578A patent/IL99578A0/xx unknown
- 1991-10-22 TW TW080108332A patent/TW221805B/zh active
-
1993
- 1993-03-17 KR KR1019930700813A patent/KR930702284A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ZA917560B (en) | 1992-09-30 |
| WO1992005151A1 (en) | 1992-04-02 |
| AU8767591A (en) | 1992-04-15 |
| IE913308A1 (en) | 1992-02-25 |
| CZ45193A3 (en) | 1994-02-16 |
| MY131049A (en) | 2007-07-31 |
| NZ239875A (en) | 1994-06-27 |
| PL296247A1 (en) | 1993-09-06 |
| IL99578A0 (en) | 1992-08-18 |
| US5288900A (en) | 1994-02-22 |
| SK21993A3 (en) | 1993-10-06 |
| AU662299B2 (en) | 1995-08-31 |
| ZW13191A1 (en) | 1992-02-05 |
| KR930702284A (ko) | 1993-09-08 |
| YU157091A (sh) | 1994-01-20 |
| CA2091245A1 (en) | 1992-03-22 |
| MX9101206A (es) | 1992-05-04 |
| PT99021A (pt) | 1992-12-31 |
| TW221805B (enExample) | 1994-03-21 |
| JPH06501269A (ja) | 1994-02-10 |
| EP0552254A1 (en) | 1993-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |