GB1464678A - 7-methoxy-6-thiatetracyclines and their preparation - Google Patents
7-methoxy-6-thiatetracyclines and their preparationInfo
- Publication number
- GB1464678A GB1464678A GB3256475A GB3256475A GB1464678A GB 1464678 A GB1464678 A GB 1464678A GB 3256475 A GB3256475 A GB 3256475A GB 3256475 A GB3256475 A GB 3256475A GB 1464678 A GB1464678 A GB 1464678A
- Authority
- GB
- United Kingdom
- Prior art keywords
- resulting
- methoxy
- treating
- reacting
- thiatetracycline
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 abstract 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000000640 hydroxylating effect Effects 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 2
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 abstract 1
- SHELADVIRCCTFN-UHFFFAOYSA-N 2,5-dimethoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(OC)C(S(Cl)(=O)=O)=C1 SHELADVIRCCTFN-UHFFFAOYSA-N 0.000 abstract 1
- SESUUAOAUZDHHP-UHFFFAOYSA-N 2,5-dimethoxybenzenethiol Chemical compound COC1=CC=C(OC)C(S)=C1 SESUUAOAUZDHHP-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- YSFIZZRFIZSROW-UHFFFAOYSA-N 2-phenyl-4h-1,3-thiazol-5-one Chemical compound S1C(=O)CN=C1C1=CC=CC=C1 YSFIZZRFIZSROW-UHFFFAOYSA-N 0.000 abstract 1
- HSHKOBVZFSNIKL-UHFFFAOYSA-N 3-(2,5-dimethoxyphenyl)sulfanylpentanedioic acid Chemical compound COC1=CC=C(OC)C(SC(CC(O)=O)CC(O)=O)=C1 HSHKOBVZFSNIKL-UHFFFAOYSA-N 0.000 abstract 1
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- LIWZNZUFZIFDLW-UHFFFAOYSA-N 4-[2-(5-hydroxy-8-methoxy-4-oxo-2,3-dihydrothiochromen-2-yl)ethylidene]-2-phenyl-1,3-thiazol-5-one Chemical compound S1C=2C(OC)=CC=C(O)C=2C(=O)CC1CC=C(C(S1)=O)N=C1C1=CC=CC=C1 LIWZNZUFZIFDLW-UHFFFAOYSA-N 0.000 abstract 1
- BQSVAMSAJQFDQF-UHFFFAOYSA-N 5-hydroxy-8-methoxy-2,3-dihydrothiochromen-4-one Chemical compound OC1=C2C(CCSC2=C(C=C1)OC)=O BQSVAMSAJQFDQF-UHFFFAOYSA-N 0.000 abstract 1
- WSUNFHMKFZQHHI-UHFFFAOYSA-N 8-methoxy-3,4-dihydro-2H-thiochromen-5-ol Chemical compound OC1=C2CCCSC2=C(C=C1)OC WSUNFHMKFZQHHI-UHFFFAOYSA-N 0.000 abstract 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- QTIOERDYSIHOPC-UHFFFAOYSA-N OC1=C(C(C2C(=C3C(C4=C(C=CC(=C4SC3CC2C1)OC)O)=O)O)=O)C(=O)N Chemical compound OC1=C(C(C2C(=C3C(C4=C(C=CC(=C4SC3CC2C1)OC)O)=O)O)=O)C(=O)N QTIOERDYSIHOPC-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 abstract 1
- LSNSJCKGQREPDW-UHFFFAOYSA-N methyl 3-amino-3-oxopropanoate Chemical compound COC(=O)CC(N)=O LSNSJCKGQREPDW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
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 |
|---|---|
| GB1464678A true GB1464678A (en) | 1977-02-16 |
Family
ID=5922377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3256475A Expired GB1464678A (en) | 1974-08-03 | 1975-08-04 | 7-methoxy-6-thiatetracyclines and their preparation |
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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1534300A4 (en) * | 2002-07-12 | 2008-04-23 | Paratek Pharm Innc | TETRACYCLINE COMPOUNDS SUBSTITUTED IN 3, 10, AND 12A |
Families Citing this family (13)
| 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 |
| DE2746044C2 (de) * | 1977-10-13 | 1979-09-06 | Merck Patent Gmbh, 6100 Darmstadt | Verfahren zur Herstellung von e-Thiatetracyclinracematen mit natürlicher Konfiguration und ihren optischen Antipoden |
| 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 |
| CN1450989A (zh) * | 2000-07-07 | 2003-10-22 | 塔夫茨大学信托人 | 7－取代的四环素化合物 |
| ATE404528T1 (de) * | 2001-03-13 | 2008-08-15 | Paratek Pharm Innc | 7,9 substituierte tetracyclinverbindungen |
| AU2005299294B2 (en) * | 2004-10-25 | 2012-06-07 | Paratek Pharmaceuticals, Inc. | 4-aminotetracyclines and methods of use thereof |
| CA2761241C (en) | 2009-05-08 | 2018-02-27 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
| CN105622496B (zh) * | 2009-08-28 | 2019-03-05 | 四相制药公司 | 四环素类化合物 |
| WO2014036502A2 (en) | 2012-08-31 | 2014-03-06 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
| KR102660864B1 (ko) | 2016-10-19 | 2024-04-25 | 테트라페이즈 파마슈티컬스, 인코포레이티드 | 에라바사이클린의 결정질 형태 |
| 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 |
|---|---|---|---|---|
| CA999855A (en) * | 1972-09-18 | 1976-11-16 | Societa' Farmaceutici Italia S.P.A. | Process for the preparation of tetracyclines derivatives in the 7 position |
-
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 FR FR7523989A patent/FR2280386A1/fr active Granted
- 1975-07-31 BE BE7000685A patent/BE832015A/xx unknown
- 1975-07-31 LU LU73113A patent/LU73113A1/xx unknown
- 1975-08-01 DD DD187631A patent/DD119426A5/xx unknown
- 1975-08-01 NL NL7509205A patent/NL7509205A/xx not_active Application Discontinuation
- 1975-08-01 AT AT600375A patent/AT344889B/de not_active IP Right Cessation
- 1975-08-01 HU HU75ME00001882A patent/HU171804B/hu unknown
- 1975-08-01 PL PL1975182476A patent/PL100508B1/pl unknown
- 1975-08-01 ES ES439927A patent/ES439927A1/es not_active Expired
- 1975-08-01 ZA ZA00754975A patent/ZA754975B/xx unknown
- 1975-08-01 IE IE1723/75A patent/IE41440B1/en unknown
- 1975-08-01 DK DK351875A patent/DK135842C/da active
- 1975-08-01 CA CA232,694A patent/CA1066710A/en not_active Expired
- 1975-08-04 GB GB3256475A patent/GB1464678A/en not_active Expired
- 1975-08-04 JP JP50095311A patent/JPS5141362A/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1534300A4 (en) * | 2002-07-12 | 2008-04-23 | Paratek Pharm Innc | TETRACYCLINE COMPOUNDS SUBSTITUTED IN 3, 10, AND 12A |
| US7825105B2 (en) | 2002-07-12 | 2010-11-02 | Paratek Pharmaceuticals, Inc. | 3, 10, and 12a substituted tetracycline compounds |
| US8481513B2 (en) | 2002-07-12 | 2013-07-09 | Paratek Pharmaceuticals, Inc. | 3, 10, and 12a substituted tetracycline compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| SE7508642L (sv) | 1976-02-04 |
| LU73113A1 (en:Method) | 1976-03-02 |
| JPS5141362A (en) | 1976-04-07 |
| DD119426A5 (en:Method) | 1976-04-20 |
| PL100508B1 (pl) | 1978-10-31 |
| AT344889B (de) | 1978-08-10 |
| HU171804B (hu) | 1978-03-28 |
| FR2280386A1 (fr) | 1976-02-27 |
| AU8360175A (en) | 1977-02-03 |
| CS191882B2 (en) | 1979-07-31 |
| US3988468A (en) | 1976-10-26 |
| ZA754975B (en) | 1976-07-28 |
| CA1066710A (en) | 1979-11-20 |
| ATA600375A (de) | 1977-12-15 |
| NL7509205A (nl) | 1976-02-05 |
| IE41440L (en) | 1976-02-03 |
| BE832015A (nl) | 1976-02-02 |
| DK135842B (da) | 1977-07-04 |
| IL47535A (en) | 1978-04-30 |
| FR2280386B1 (en:Method) | 1979-10-12 |
| ES439927A1 (es) | 1977-06-01 |
| IE41440B1 (en) | 1980-01-02 |
| DK351875A (da) | 1976-02-04 |
| DK135842C (da) | 1977-11-28 |
| IL47535A0 (en) | 1975-08-31 |
| DE2437487A1 (de) | 1976-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |