FI69473C - Foerfarande foer framstaellning av terapeutiskt anvaendbara deivat av erytromycin - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara deivat av erytromycin Download PDFInfo
- Publication number
- FI69473C FI69473C FI810042A FI810042A FI69473C FI 69473 C FI69473 C FI 69473C FI 810042 A FI810042 A FI 810042A FI 810042 A FI810042 A FI 810042A FI 69473 C FI69473 C FI 69473C
- Authority
- FI
- Finland
- Prior art keywords
- group
- formula
- compound
- erythromycin
- oxime
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 15
- 230000001225 therapeutic effect Effects 0.000 title 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 170
- -1 alkaline earth metal carbonate Chemical class 0.000 claims description 106
- 229960003276 erythromycin Drugs 0.000 claims description 83
- 239000000203 mixture Substances 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 61
- KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\O)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 claims description 43
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 40
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 40
- 239000012312 sodium hydride Substances 0.000 claims description 40
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 40
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 21
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 21
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 21
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
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- 229910052736 halogen Inorganic materials 0.000 claims description 11
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- 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 claims description 10
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 claims description 10
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- 235000005985 organic acids Nutrition 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
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- 125000002252 acyl group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 235000011181 potassium carbonates Nutrition 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 4
- 235000015424 sodium Nutrition 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 235000001465 calcium Nutrition 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000012434 nucleophilic reagent Substances 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
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- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 230000000007 visual effect Effects 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 claims 1
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 88
- 150000002923 oximes Chemical class 0.000 description 64
- 239000000243 solution Substances 0.000 description 63
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 49
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- 238000004458 analytical method Methods 0.000 description 46
- 238000003756 stirring Methods 0.000 description 46
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- 239000002244 precipitate Substances 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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- CYLJJGWXJNNBDU-UHFFFAOYSA-N 2-[2,3-bis(2-aminoethyl)phenyl]ethanamine Chemical compound NCCC1=CC=CC(CCN)=C1CCN CYLJJGWXJNNBDU-UHFFFAOYSA-N 0.000 description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8000566 | 1980-01-11 | ||
| FR8000566A FR2473525A1 (fr) | 1980-01-11 | 1980-01-11 | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI810042L FI810042L (fi) | 1981-07-12 |
| FI69473B FI69473B (fi) | 1985-10-31 |
| FI69473C true FI69473C (fi) | 1986-02-10 |
Family
ID=9237443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI810042A FI69473C (fi) | 1980-01-11 | 1981-01-08 | Foerfarande foer framstaellning av terapeutiskt anvaendbara deivat av erytromycin |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4349545A (en, 2012) |
| EP (1) | EP0033255B1 (en, 2012) |
| JP (1) | JPS56100799A (en, 2012) |
| KR (1) | KR850000964B1 (en, 2012) |
| AU (1) | AU537247B2 (en, 2012) |
| BG (1) | BG61369B2 (en, 2012) |
| CA (1) | CA1162535A (en, 2012) |
| CY (1) | CY1319A (en, 2012) |
| DE (1) | DE3165720D1 (en, 2012) |
| DK (1) | DK157878C (en, 2012) |
| ES (1) | ES8200702A1 (en, 2012) |
| FI (1) | FI69473C (en, 2012) |
| FR (1) | FR2473525A1 (en, 2012) |
| GR (1) | GR73103B (en, 2012) |
| GT (1) | GT198500080A (en, 2012) |
| HK (1) | HK586A (en, 2012) |
| HU (1) | HU187760B (en, 2012) |
| IE (1) | IE50680B1 (en, 2012) |
| IL (1) | IL61808A (en, 2012) |
| LU (1) | LU88283I2 (en, 2012) |
| MY (1) | MY8500984A (en, 2012) |
| NL (1) | NL930097I2 (en, 2012) |
| OA (1) | OA06719A (en, 2012) |
| PT (1) | PT72331B (en, 2012) |
| ZA (1) | ZA808108B (en, 2012) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2534588B2 (fr) * | 1982-10-15 | 1985-09-20 | Roussel Uclaf | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| US4526889A (en) * | 1982-11-15 | 1985-07-02 | Pfizer Inc. | Epimeric azahomoerythromycin A derivative, intermediates and method of use |
| DK149776C (da) * | 1984-01-06 | 1987-04-21 | Orion Yhtymae Oy | Antibiotisk virksom erytromycinforbindelse og praeparat indeholdende forbindelsen |
| JPS60214796A (ja) * | 1984-04-06 | 1985-10-28 | Taisho Pharmaceut Co Ltd | ６−０−メチルエリスロマイシン類の製法 |
| JPS61103890A (ja) * | 1984-10-26 | 1986-05-22 | Taisho Pharmaceut Co Ltd | ６−０−メチルエリスロマイシンａ誘導体 |
| US4847242A (en) | 1985-03-12 | 1989-07-11 | Beecham Group P.L.C. | 11-ether derivatives of erythromycins |
| JPS61229895A (ja) * | 1985-04-03 | 1986-10-14 | Nippon Zeon Co Ltd | 保護化デス−ｎ−メチルエリスロマイシン誘導体 |
| US4740502A (en) * | 1986-06-20 | 1988-04-26 | Abbott Laboratories | Semisynthetic erythromycin antibiotics |
| DE3782994T2 (de) | 1986-09-18 | 1993-04-08 | Taisho Pharma Co Ltd | Erythromycin-a-derivate und verfahren zu ihrer herstellung. |
| JP2751385B2 (ja) * | 1988-05-19 | 1998-05-18 | 大正製薬株式会社 | エリスロマイシンａオキシム及びその塩の製造方法 |
| US5075289A (en) * | 1988-06-07 | 1991-12-24 | Abbott Laboratories | 9-r-azacyclic erythromycin antibiotics |
| US5302705A (en) * | 1989-10-07 | 1994-04-12 | Taisho Pharmaceutical Co., Ltd. | 6-O-methylerythromycin a oxime derivatives |
| US5912331A (en) * | 1991-03-15 | 1999-06-15 | Merck & Co., Inc. | Process for the preparation of 9-deoxo-9(Z)-hydroxyiminoerythromycin A |
| DE69227713D1 (de) | 1991-03-15 | 1999-01-14 | Merck & Co Inc | 9-Deoxo-9(Z)-hydroxyiminoerythromycin A und O-Derivate hiervon |
| US5985844A (en) * | 1992-03-26 | 1999-11-16 | Merck & Co., Inc. | Homoerythromycin A derivatives modified at the 4"-and 8A-positions |
| US5189159A (en) * | 1992-04-02 | 1993-02-23 | Merck & Co., Inc. | 8a-AZA-8a-homoerythromycin cyclic iminoethers |
| ES2036472B1 (es) * | 1991-10-01 | 1994-03-01 | Prodesfarma Sa | Procedimiento de obtencion de eritromicina 9-(0-((2-metoxietoxi)metil)oxima) (roxitromicina). |
| US5210235A (en) * | 1992-08-26 | 1993-05-11 | Merck & Co., Inc. | Methods of elaborating erythromycin fragments into amine-containing fragments of azalide antibiotics |
| US5332807A (en) * | 1993-04-14 | 1994-07-26 | Merck & Co., Inc. | Process of producing 8A- and 9A-azalide antibiotics |
| US5795871A (en) * | 1994-04-26 | 1998-08-18 | Nobuhiro Narita | Pharmaceutical composition for treatment of non-small cell lung cancer |
| IT1276901B1 (it) * | 1994-12-13 | 1997-11-03 | Zambon Spa | Derivati dell'eritromicina a 9-0-ossina dotati di attivita' antibiotica |
| US5872229A (en) | 1995-11-21 | 1999-02-16 | Abbott Laboratories | Process for 6-O-alkylation of erythromycin derivatives |
| FR2760017B1 (fr) * | 1997-02-27 | 1999-04-30 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erytromycine, leur procede de preparation et leur application comme medicaments |
| US5929219A (en) | 1997-09-10 | 1999-07-27 | Abbott Laboratories | 9-hydrazone and 9-azine erythromycin derivatives and a process of making the same |
| PT102202B (pt) | 1998-09-10 | 2001-04-30 | Hovione Sociedade Quimica S A | Processo para a purificacao de roxitromicina |
| IN190782B (en, 2012) * | 1998-09-30 | 2003-08-23 | Max India Ltd | |
| DE69813244T2 (de) * | 1998-11-24 | 2004-03-04 | Jubilant Organosys Ltd. | Verfahren zur Herstellung von Roxithromycin und Derivate davon |
| CZ20021999A3 (cs) | 1999-12-16 | 2003-02-12 | Teva Pharmaceutical Industries Ltd. | Způsob přípravy klaritromycinových polymorfních forem a nového polymorfu IV |
| IL150698A0 (en) * | 2000-01-11 | 2003-02-12 | Teva Pharma | Processes for preparing clarithromycin polymorphs |
| WO2001064224A1 (en) | 2000-02-29 | 2001-09-07 | Teva Pharmaceutical Industries Ltd. | Processes for preparing clarithromycin and clarithromycin intermediate, essentially oxime-free clarithromycin, and pharmaceutical composition comprising the same |
| HRP20020885B1 (en) | 2002-11-11 | 2007-05-31 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | SUBSTITUTED 9a-N-{N'-[4-(SULFONYL)PHENYLCARBAMOYL]}DERIVATIVES 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHROMYCIN A AND 5-O-DESOZAMINYL-9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHRONOLIDE A |
| HRP20020991A2 (en) | 2002-12-12 | 2005-02-28 | Pliva-Istra�iva�ki institut d.o.o. | N"-Substituted 9a-N-(N'-carbamoyl-Gamma-aminopropyl), 9a-N-(N'? -thiocarbamoyl-Gamma-aminopropyl), 9a-N-(N'-((Beta-cyanoethyl)-N'-carbamoyl-Gamma? -aminopropyl) and 9a-N-(N'-(Beta-cyanoethyl)-N'-thiocarbamoyl-Gamma? -aminopropyl) derivatives of 9-de |
| EP1435359A1 (en) * | 2002-12-31 | 2004-07-07 | Alembic Limited | A process for the purification of roxithromycin |
| RU2222333C1 (ru) * | 2003-03-06 | 2004-01-27 | Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин" | Фармацевтическая композиция с антибактериальной активностью и способ ее получения |
| KR20090042971A (ko) | 2006-08-24 | 2009-05-04 | 욱크하르트 리서치 센터 | 항미생물 활성을 갖는 신규한 마크로라이드 및 케토라이드 |
| US20090005326A1 (en) * | 2007-06-26 | 2009-01-01 | Idexx Laboratories, Inc. | Single dose roxithromycin |
| CA2820451C (en) | 2010-12-09 | 2017-12-12 | Wockhardt Limited | Ketolide compounds |
| EP2681222B1 (en) | 2011-03-01 | 2018-02-28 | Wockhardt Limited | Process for preparation of ketolide intermediates |
| CA2830861C (en) | 2011-03-22 | 2017-01-24 | Wockhardt Limited | Process for preparation of ketolide compounds |
| CN102219816A (zh) * | 2011-05-12 | 2011-10-19 | 浙江国邦药业有限公司 | 一种罗红霉素的纯化方法 |
| PL222631B1 (pl) | 2012-11-14 | 2016-08-31 | Gdański Univ Medyczny | Kompozycja farmaceutyczna zawierająca roksytromycynę, sposób jej wytwarzania oraz zastosowanie medyczne tej kompozycji i produkt leczniczy zawierający kompozycję |
| CN104163840A (zh) * | 2013-08-30 | 2014-11-26 | 郑州后羿制药有限公司 | 一种罗红霉素的精制方法 |
| FR3049861A1 (fr) | 2016-04-07 | 2017-10-13 | Univ Claude Bernard Lyon | Nouvelles compositions antivirales pour le traitement de la grippe |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU31319B (en) * | 1967-08-03 | 1973-04-30 | Pliva Pharm & Chem Works | Postupak za dobijanje acil derivata eritromicin oksima |
| US3869444A (en) * | 1972-10-10 | 1975-03-04 | Abbott Lab | Esters of erythromycin oxime |
| ES434842A1 (es) * | 1975-02-19 | 1976-12-01 | Andreu Sa Dr | Procedimiento para la preparacion de esteres de la oxima deeritromicina. |
| DE2515077A1 (de) * | 1975-04-07 | 1976-10-28 | Thomae Gmbh Dr K | Neue 9-alkylidenamino-erythromycine, ihre salze und verfahren zu ihrer herstellung |
| DE2515076A1 (de) * | 1975-04-07 | 1976-10-28 | Thomae Gmbh Dr K | Neue erythromycinderivate, deren salze und verfahren zu ihrer herstellung |
| DK139522C (da) * | 1975-04-07 | 1979-08-20 | Thomae Gmbh Dr K | Analogifremgangsmaade til fremstilling af 9-iminoalkylamino-erythromyciner eller syreadditionssalte deraf |
| DE2750288A1 (de) * | 1977-11-10 | 1979-05-17 | Thomae Gmbh Dr K | Neue 9-(omega-heteroarylamino- alkylamino)-erythromycine, ihre salze, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
-
1980
- 1980-01-11 FR FR8000566A patent/FR2473525A1/fr active Granted
- 1980-12-26 IL IL61808A patent/IL61808A/xx not_active IP Right Cessation
- 1980-12-30 ZA ZA00808108A patent/ZA808108B/xx unknown
-
1981
- 1981-01-08 US US06/223,368 patent/US4349545A/en not_active Expired - Lifetime
- 1981-01-08 FI FI810042A patent/FI69473C/fi not_active IP Right Cessation
- 1981-01-09 DE DE8181400026T patent/DE3165720D1/de not_active Expired
- 1981-01-09 DK DK007881A patent/DK157878C/da active
- 1981-01-09 HU HU8155A patent/HU187760B/hu unknown
- 1981-01-09 CA CA000368249A patent/CA1162535A/fr not_active Expired
- 1981-01-09 JP JP126481A patent/JPS56100799A/ja active Granted
- 1981-01-09 EP EP81400026A patent/EP0033255B1/fr not_active Expired
- 1981-01-09 CY CY1319A patent/CY1319A/xx unknown
- 1981-01-09 ES ES498395A patent/ES8200702A1/es not_active Expired
- 1981-01-09 OA OA57295A patent/OA06719A/xx unknown
- 1981-01-09 GR GR63831A patent/GR73103B/el unknown
- 1981-01-09 PT PT72331A patent/PT72331B/pt unknown
- 1981-01-09 AU AU66131/81A patent/AU537247B2/en not_active Expired
- 1981-01-09 IE IE46/81A patent/IE50680B1/en not_active IP Right Cessation
- 1981-01-10 KR KR1019810000051A patent/KR850000964B1/ko not_active Expired
-
1985
- 1985-09-12 GT GT198500080A patent/GT198500080A/es unknown
- 1985-12-30 MY MY984/85A patent/MY8500984A/xx unknown
-
1986
- 1986-01-02 HK HK5/86A patent/HK586A/xx not_active IP Right Cessation
-
1993
- 1993-06-03 LU LU88283C patent/LU88283I2/fr unknown
- 1993-06-25 NL NL930097C patent/NL930097I2/nl unknown
-
1994
- 1994-02-22 BG BG098506A patent/BG61369B2/bg unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Transfer of assignment of patent |
Owner name: HOECHST MARION ROUSSEL |
|
| MA | Patent expired |
Owner name: HOECHST MARION ROUSSEL |