LT3274B - Process for preparing 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid - Google Patents
Process for preparing 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid Download PDFInfo
- Publication number
- LT3274B LT3274B LTIP510A LTIP510A LT3274B LT 3274 B LT3274 B LT 3274B LT IP510 A LTIP510 A LT IP510A LT IP510 A LTIP510 A LT IP510A LT 3274 B LT3274 B LT 3274B
- Authority
- LT
- Lithuania
- Prior art keywords
- dihydroquinoline
- oxo
- carboxylic acid
- piperazinyl
- fluoro
- Prior art date
Links
- -1 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid Chemical class 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 125000004494 ethyl ester group Chemical group 0.000 abstract description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 230000003595 spectral effect Effects 0.000 description 8
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 125000004193 piperazinyl group Chemical group 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- SIZQHYOHXHCYHI-UHFFFAOYSA-N 1-cyclopropyl-7-(4-ethoxycarbonylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C(=O)OCC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SIZQHYOHXHCYHI-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OIAHODUMUYMPHR-UHFFFAOYSA-N CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCN(CC3)C(=O)OCC)F)C(=O)OCC Chemical compound CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCN(CC3)C(=O)OCC)F)C(=O)OCC OIAHODUMUYMPHR-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- GZDOLMHJYOJBDF-UHFFFAOYSA-N 6-fluoro-1-(2-hydroxyethyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C1=C2N(CCO)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 GZDOLMHJYOJBDF-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- GGWLGDBEMJWMAH-UHFFFAOYSA-N ethyl 1-cyclopropyl-7-(4-ethoxycarbonylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylate Chemical compound C(C)OC(=O)C1=CN(C2=CC(=C(C=C2C1=O)F)N1CCN(CC1)C(=O)OCC)C1CC1 GGWLGDBEMJWMAH-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RSAMZLZRMSYMNT-UHFFFAOYSA-N 7-(4-ethoxycarbonylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound CCOC(=O)N1CCN(CC1)c1cc2n(CC)cc(C(O)=O)c(=O)c2cc1F RSAMZLZRMSYMNT-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- CHBYWZMBAWPPHO-UHFFFAOYSA-N ethyl 1-ethyl-6,7-difluoro-4-oxoquinoline-3-carboxylate Chemical compound FC1=C(F)C=C2C(=O)C(C(=O)OCC)=CN(CC)C2=C1 CHBYWZMBAWPPHO-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Chemical group 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU244787A YU46099B (sh) | 1987-12-31 | 1987-12-31 | Postopek za pripravo 1-supstituirane 6-fluoro-4-okso-7- 1-piperazinil)-1 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP510A LTIP510A (en) | 1994-11-25 |
| LT3274B true LT3274B (en) | 1995-05-25 |
Family
ID=25557985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP510A LT3274B (en) | 1987-12-31 | 1993-05-05 | Process for preparing 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT396105B (cs) |
| CS (1) | CS274635B2 (cs) |
| DD (1) | DD283386B5 (cs) |
| HU (1) | HU200454B (cs) |
| LT (1) | LT3274B (cs) |
| LV (1) | LV10774B (cs) |
| NO (1) | NO885666L (cs) |
| PL (1) | PL163337B1 (cs) |
| PT (1) | PT89359B (cs) |
| RU (1) | RU2002744C1 (cs) |
| SI (1) | SI8712447A8 (cs) |
| YU (1) | YU46099B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI9200377A (en) * | 1992-12-11 | 1994-06-30 | Krka | Process for the preparation of 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxilic acid, novel intermediate used in this process and process for its preparation |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2840910A1 (de) | 1977-09-20 | 1979-04-05 | Bellon Labor Sa Roger | 7-dialkylamino-6-halogen-4-oxo-1,4- dihydro-3-chinolin-carbonsaeuren, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
| BE890223A (fr) | 1980-09-05 | 1982-01-04 | Kyorin Seiyaku Kk | Procede de preparation de derives de l'acide quinoleine-carboxylique |
| DE3308909A1 (de) | 1983-03-12 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Bakterizide mittel auf chinoloncarbonsaeure-basis |
| JPH033453A (ja) | 1989-05-31 | 1991-01-09 | Nippon Telegr & Teleph Corp <Ntt> | パケット交換網用ルーチング方法 |
| JPH066686A (ja) | 1992-06-17 | 1994-01-14 | Ricoh Co Ltd | 撮像装置 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017622A (en) * | 1972-12-18 | 1977-04-12 | Dainippon Pharmaceutical Co., Ltd. | Piperazine derivatives |
| JPS5845426B2 (ja) * | 1978-09-29 | 1983-10-08 | 杏林製薬株式会社 | 置換キノリンカルボン酸誘導体 |
| DE3306771A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3509546A1 (de) * | 1985-03-16 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | 7-amino-1-(subst.cyclopropyl)-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
-
1987
- 1987-12-31 YU YU244787A patent/YU46099B/sh unknown
- 1987-12-31 SI SI8712447A patent/SI8712447A8/sl unknown
-
1988
- 1988-12-21 NO NO88885666A patent/NO885666L/no unknown
- 1988-12-28 PT PT8935988A patent/PT89359B/pt not_active IP Right Cessation
- 1988-12-29 CS CS903288A patent/CS274635B2/cs unknown
- 1988-12-30 HU HU667788A patent/HU200454B/hu not_active IP Right Cessation
- 1988-12-30 AT AT320688A patent/AT396105B/de not_active IP Right Cessation
- 1988-12-30 PL PL27689088A patent/PL163337B1/pl unknown
- 1988-12-30 DD DD32470388A patent/DD283386B5/de active IP Right Maintenance
- 1988-12-30 RU SU4613227 patent/RU2002744C1/ru active
-
1993
- 1993-05-05 LT LTIP510A patent/LT3274B/lt not_active IP Right Cessation
- 1993-06-30 LV LVP-93-828A patent/LV10774B/lv unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2840910A1 (de) | 1977-09-20 | 1979-04-05 | Bellon Labor Sa Roger | 7-dialkylamino-6-halogen-4-oxo-1,4- dihydro-3-chinolin-carbonsaeuren, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
| BE890223A (fr) | 1980-09-05 | 1982-01-04 | Kyorin Seiyaku Kk | Procede de preparation de derives de l'acide quinoleine-carboxylique |
| DE3308909A1 (de) | 1983-03-12 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Bakterizide mittel auf chinoloncarbonsaeure-basis |
| JPH033453A (ja) | 1989-05-31 | 1991-01-09 | Nippon Telegr & Teleph Corp <Ntt> | パケット交換網用ルーチング方法 |
| JPH066686A (ja) | 1992-06-17 | 1994-01-14 | Ricoh Co Ltd | 撮像装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| HU200454B (en) | 1990-06-28 |
| LTIP510A (en) | 1994-11-25 |
| YU46099B (sh) | 1992-12-21 |
| LV10774A (lv) | 1995-08-20 |
| HUT49129A (en) | 1989-08-28 |
| PT89359B (pt) | 1993-08-31 |
| NO885666L (no) | 1989-07-03 |
| NO885666D0 (no) | 1988-12-21 |
| YU244787A (en) | 1990-06-30 |
| LV10774B (en) | 1996-08-20 |
| PL163337B1 (pl) | 1994-03-31 |
| PT89359A (pt) | 1989-12-29 |
| DD283386B5 (de) | 1997-10-30 |
| CS903288A2 (en) | 1990-12-13 |
| RU2002744C1 (ru) | 1993-11-15 |
| SI8712447A8 (en) | 1995-12-31 |
| ATA320688A (de) | 1992-10-15 |
| PL276890A1 (en) | 1989-10-16 |
| CS274635B2 (en) | 1991-09-15 |
| AT396105B (de) | 1993-06-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR870000892B1 (ko) | 퀴놀론카복실산의 제조방법 | |
| CA1340285C (en) | Novel quinolonecarboxylic acid derivatives having at 7-position a piperidin-1-yl substituent | |
| KR950010325B1 (ko) | 4-옥소퀴놀린-3-카르복실산 유도체, 그의 제조방법 | |
| KR940007305B1 (ko) | 8-위치에서 치환된 퀴놀론카복실산 유도체, 이의 제조방법 및 이를 함유하는 약제학적 조성물 | |
| HU187580B (en) | Process for producing 1-cyclopropy-6-fluoro-1,4-dihydro-4-oxo-7-piperazino-quinoline-3-carboxylic acid derivatives and antibacterial compositions containing them as active agents | |
| JPH0581590B2 (cs) | ||
| JP2532192B2 (ja) | １−アミノ−２−フルオロシクロプロパン | |
| US4559342A (en) | Quinolone acids and antibacterial agents containing these compounds | |
| US4686221A (en) | Quinolinecarboxylic acid compounds and antimicrobial agent containing the same | |
| EP0187376B1 (de) | 6,7-Disubstituierte 1-Cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridin-3-carbonsäuren | |
| JPS61205258A (ja) | キノロンカルボン酸誘導体及びその製造方法 | |
| US4563448A (en) | Bactericidal agents | |
| KR100256461B1 (ko) | 삼환 화합물의 제조 방법 | |
| US5914401A (en) | Methods for the manufacture of quinolone carboxylic acids derivatives and intermediates thereof | |
| LT3274B (en) | Process for preparing 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid | |
| KR870000894B1 (ko) | 퀴놀론 카복실산의 제조방법 | |
| RU2127270C1 (ru) | Способ получения 1-замещенной-6-фтор-4-оксо-7-(1-пиперазинил)-1,4-дигидро-хинолин-3- карбоновой кислоты, 1-замещенной-6-фтор-4-оксо-7-(4-замещенной-1-пиперазинил)-1,4- дигидрохинолин-3-карбоксилат-бор-диацетат и способ его получения | |
| JP2825641B2 (ja) | キノリンカルボン酸誘導体の製造方法 | |
| JPS647072B2 (cs) | ||
| KR870000893B1 (ko) | 퀴놀론 카복실산의 제조방법 | |
| JPH05112554A (ja) | 新規なキノロンカルボン酸誘導体 | |
| JP2598737B2 (ja) | 選択毒性に優れた８−アルコキシキノロンカルボン酸およびその塩並びにその製造方法 | |
| JP3523874B2 (ja) | 中間体としてのキノロン二硫化物 | |
| DD283385A5 (de) | Verfahren zur herstellung von derivaten der 7-(1-azetidinyl)-1,4-dihydro-4-oxoquinolein-3-carboxylsaeure | |
| KR0139261B1 (ko) | 피리돈 카르복실산 항균체 및 이의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 19980505 |