DE2437487A1 - 7-methoxy-6-thia-tetracycline und verfahren zu ihrer herstellung - Google Patents
7-methoxy-6-thia-tetracycline und verfahren zu ihrer herstellungInfo
- Publication number
- DE2437487A1 DE2437487A1 DE2437487A DE2437487A DE2437487A1 DE 2437487 A1 DE2437487 A1 DE 2437487A1 DE 2437487 A DE2437487 A DE 2437487A DE 2437487 A DE2437487 A DE 2437487A DE 2437487 A1 DE2437487 A1 DE 2437487A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- thia
- methoxy
- formula
- tetracycline
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000004098 Tetracycline Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229960002180 tetracycline Drugs 0.000 claims description 8
- 239000002168 alkylating agent Substances 0.000 claims description 6
- 229940100198 alkylating agent Drugs 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 241000534944 Thia Species 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
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- 238000003756 stirring Methods 0.000 description 14
- -1 phenoxypropyl radical Chemical class 0.000 description 11
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- 239000007858 starting material Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
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- 125000002252 acyl group Chemical class 0.000 description 5
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- 239000003814 drug Substances 0.000 description 5
- 238000007327 hydrogenolysis reaction Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 235000012222 talc Nutrition 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 229930101283 tetracycline Natural products 0.000 description 4
- 229940040944 tetracyclines Drugs 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
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- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
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- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 235000008160 pyridoxine Nutrition 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
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- 229960002477 riboflavin Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- GLBQVJGBPFPMMV-UHFFFAOYSA-N sulfilimine Chemical class S=N GLBQVJGBPFPMMV-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2437487A DE2437487A1 (de) | 1974-08-03 | 1974-08-03 | 7-methoxy-6-thia-tetracycline und verfahren zu ihrer herstellung |
| IL47535A IL47535A (en) | 1974-08-03 | 1975-06-20 | 7-methoxy-6-thiatetracyclines and their preparation |
| CS754878A CS191882B2 (en) | 1974-08-03 | 1975-07-09 | Method of preparing 7-methoxy-6-thia-tetracycline |
| US05/600,377 US3988468A (en) | 1974-08-03 | 1975-07-30 | 7-Methoxy-6-thiatetracyclines and their preparation |
| SE7508642A SE7508642L (sv) | 1974-08-03 | 1975-07-30 | 7-metoxi-6-tia-tetracykliner och forfarande for framstellning derav |
| BE7000685A BE832015A (nl) | 1974-08-03 | 1975-07-31 | Werkwijze voor het bereiden van 7-methoxy-6-thiatetracyclinen |
| FR7523989A FR2280386A1 (fr) | 1974-08-03 | 1975-07-31 | 7-methoxy-6-thia-tetracyclines et leur procede de preparation |
| LU73113A LU73113A1 (en:Method) | 1974-08-03 | 1975-07-31 | |
| ES439927A ES439927A1 (es) | 1974-08-03 | 1975-08-01 | Procedimiento para la obtencion de 7-metoxi-6-tiatetracicli-nas. |
| ZA00754975A ZA754975B (en) | 1974-08-03 | 1975-08-01 | 7-methoxy-6-thiatetracyclines and their preparation |
| HU75ME00001882A HU171804B (hu) | 1974-08-03 | 1975-08-01 | Sposob poluchenija proizvodnykh 7-metoksi-6-tiatetraciklina |
| AT600375A AT344889B (de) | 1974-08-03 | 1975-08-01 | Verfahren zur herstellung von neuen 7-methoxy-6-thiatetracyclinen und deren salzen |
| PL1975182476A PL100508B1 (pl) | 1974-08-03 | 1975-08-01 | Sposob wytwarzania nowych 7-metoksy-6-tiatetracyklin |
| DD187631A DD119426A5 (en:Method) | 1974-08-03 | 1975-08-01 | |
| NL7509205A NL7509205A (nl) | 1974-08-03 | 1975-08-01 | Werkwijze voor het bereiden van 7-methoxy-6- -thiatetracyclinen. |
| DK351875A DK135842C (da) | 1974-08-03 | 1975-08-01 | Analogifremgangsmade til fremstilling af 7-methoxy-6-thiatetracycliner eller syreadditionssalte deraf |
| AU83601/75A AU495105B2 (en) | 1974-08-03 | 1975-08-01 | 7-methoxy-6-thia-tetracyclines and their preparation |
| CA232,694A CA1066710A (en) | 1974-08-03 | 1975-08-01 | 7-methoxy-6-thiatetracyclines and their preparation |
| IE1723/75A IE41440B1 (en) | 1974-08-03 | 1975-08-01 | 7-methoxy-6-thiatetracyclines and their preparation |
| JP50095311A JPS5141362A (en) | 1974-08-03 | 1975-08-04 | 77 metokishi 66 chiatetorasaikurinrui oyobi sonoseizohoho |
| GB3256475A GB1464678A (en) | 1974-08-03 | 1975-08-04 | 7-methoxy-6-thiatetracyclines and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2437487A DE2437487A1 (de) | 1974-08-03 | 1974-08-03 | 7-methoxy-6-thia-tetracycline und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2437487A1 true DE2437487A1 (de) | 1976-02-19 |
Family
ID=5922377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2437487A Withdrawn DE2437487A1 (de) | 1974-08-03 | 1974-08-03 | 7-methoxy-6-thia-tetracycline und verfahren zu ihrer herstellung |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3988468A (en:Method) |
| JP (1) | JPS5141362A (en:Method) |
| AT (1) | AT344889B (en:Method) |
| BE (1) | BE832015A (en:Method) |
| CA (1) | CA1066710A (en:Method) |
| CS (1) | CS191882B2 (en:Method) |
| DD (1) | DD119426A5 (en:Method) |
| DE (1) | DE2437487A1 (en:Method) |
| DK (1) | DK135842C (en:Method) |
| ES (1) | ES439927A1 (en:Method) |
| FR (1) | FR2280386A1 (en:Method) |
| GB (1) | GB1464678A (en:Method) |
| HU (1) | HU171804B (en:Method) |
| IE (1) | IE41440B1 (en:Method) |
| IL (1) | IL47535A (en:Method) |
| LU (1) | LU73113A1 (en:Method) |
| NL (1) | NL7509205A (en:Method) |
| PL (1) | PL100508B1 (en:Method) |
| SE (1) | SE7508642L (en:Method) |
| ZA (1) | ZA754975B (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001558A1 (de) * | 1977-10-13 | 1979-05-02 | MERCK PATENT GmbH | Verfahren zur Herstellung von 6-Thiatetracyclinracematen mit "natürlicher Konfiguration" und ihren optischen Antipoden |
| EP2301912A3 (en) * | 2004-10-25 | 2012-07-11 | Paratek Pharmaceuticals, Inc. | 4-aminotetracyclines and methods of use thereof |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2442829A1 (de) * | 1974-09-06 | 1976-03-18 | Merck Patent Gmbh | Tetracyclische verbindungen und verfahren zu ihrer herstellung |
| JPS5845093A (ja) * | 1981-09-11 | 1983-03-16 | Kobe Steel Ltd | 平版用印刷基板 |
| JPS60196396A (ja) * | 1984-03-21 | 1985-10-04 | Ube Ind Ltd | 平版印刷板用基材 |
| KR100997596B1 (ko) * | 2000-07-07 | 2010-11-30 | 파라테크 파마슈티컬스, 인크. | 7-치환 테트라사이클린 화합물 |
| EP2301913A1 (en) * | 2001-03-13 | 2011-03-30 | Paratek Pharmaceuticals, Inc. | 7,9-Substituted tetracycline compounds |
| CN1700922A (zh) * | 2002-07-12 | 2005-11-23 | 帕拉特克药品公司 | 3、10或12a位取代的四环素化合物 |
| CN107021887A (zh) | 2009-05-08 | 2017-08-08 | 四相制药公司 | 四环素类化合物 |
| PL2470500T3 (pl) * | 2009-08-28 | 2018-03-30 | Tetraphase Pharmaceuticals, Inc. | Związki tetracyklinowe |
| EA031523B1 (ru) | 2012-08-31 | 2019-01-31 | Тетрафейз Фармасьютикалс, Инк. | Тетрациклиновые соединения |
| SI3529236T1 (sl) | 2016-10-19 | 2024-08-30 | Tetraphase Pharmaceuticals, Inc. | Kristalinične oblike eravaciklina |
| CN109574868B (zh) * | 2018-12-28 | 2021-11-16 | 天津阿尔塔科技有限公司 | 一种四环素类及其差向异构体氘代内标物的制备方法 |
| CN111518115A (zh) * | 2020-04-15 | 2020-08-11 | 南京欧纳壹有机光电有限公司 | 硫醚取代的2-噻唑啉-4-酮封端的有机半导体化合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL158172B (nl) * | 1972-09-18 | 1978-10-16 | Farmaceutici Italia | Werkwijze voor het bereiden van tetracyclinederivaten met een substituent op de 7-plaats. |
-
1974
- 1974-08-03 DE DE2437487A patent/DE2437487A1/de not_active Withdrawn
-
1975
- 1975-06-20 IL IL47535A patent/IL47535A/xx unknown
- 1975-07-09 CS CS754878A patent/CS191882B2/cs unknown
- 1975-07-30 US US05/600,377 patent/US3988468A/en not_active Expired - Lifetime
- 1975-07-30 SE SE7508642A patent/SE7508642L/xx unknown
- 1975-07-31 LU LU73113A patent/LU73113A1/xx unknown
- 1975-07-31 BE BE7000685A patent/BE832015A/xx unknown
- 1975-07-31 FR FR7523989A patent/FR2280386A1/fr active Granted
- 1975-08-01 AT AT600375A patent/AT344889B/de not_active IP Right Cessation
- 1975-08-01 CA CA232,694A patent/CA1066710A/en not_active Expired
- 1975-08-01 NL NL7509205A patent/NL7509205A/xx not_active Application Discontinuation
- 1975-08-01 ZA ZA00754975A patent/ZA754975B/xx unknown
- 1975-08-01 DK DK351875A patent/DK135842C/da active
- 1975-08-01 PL PL1975182476A patent/PL100508B1/pl unknown
- 1975-08-01 HU HU75ME00001882A patent/HU171804B/hu unknown
- 1975-08-01 ES ES439927A patent/ES439927A1/es not_active Expired
- 1975-08-01 IE IE1723/75A patent/IE41440B1/en unknown
- 1975-08-01 DD DD187631A patent/DD119426A5/xx unknown
- 1975-08-04 JP JP50095311A patent/JPS5141362A/ja active Pending
- 1975-08-04 GB GB3256475A patent/GB1464678A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001558A1 (de) * | 1977-10-13 | 1979-05-02 | MERCK PATENT GmbH | Verfahren zur Herstellung von 6-Thiatetracyclinracematen mit "natürlicher Konfiguration" und ihren optischen Antipoden |
| EP2301912A3 (en) * | 2004-10-25 | 2012-07-11 | Paratek Pharmaceuticals, Inc. | 4-aminotetracyclines and methods of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US3988468A (en) | 1976-10-26 |
| IL47535A (en) | 1978-04-30 |
| HU171804B (hu) | 1978-03-28 |
| AT344889B (de) | 1978-08-10 |
| DK135842B (da) | 1977-07-04 |
| NL7509205A (nl) | 1976-02-05 |
| DK135842C (da) | 1977-11-28 |
| JPS5141362A (en) | 1976-04-07 |
| GB1464678A (en) | 1977-02-16 |
| DD119426A5 (en:Method) | 1976-04-20 |
| ATA600375A (de) | 1977-12-15 |
| CS191882B2 (en) | 1979-07-31 |
| ZA754975B (en) | 1976-07-28 |
| CA1066710A (en) | 1979-11-20 |
| IE41440B1 (en) | 1980-01-02 |
| FR2280386A1 (fr) | 1976-02-27 |
| PL100508B1 (pl) | 1978-10-31 |
| FR2280386B1 (en:Method) | 1979-10-12 |
| IE41440L (en) | 1976-02-03 |
| AU8360175A (en) | 1977-02-03 |
| ES439927A1 (es) | 1977-06-01 |
| IL47535A0 (en) | 1975-08-31 |
| DK351875A (da) | 1976-02-04 |
| BE832015A (nl) | 1976-02-02 |
| SE7508642L (sv) | 1976-02-04 |
| LU73113A1 (en:Method) | 1976-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |