DE1811150A1 - Tetracyclin- und Adamantan-Derivate und Verfahren zu ihrer Herstellung - Google Patents
Tetracyclin- und Adamantan-Derivate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1811150A1 DE1811150A1 DE19681811150 DE1811150A DE1811150A1 DE 1811150 A1 DE1811150 A1 DE 1811150A1 DE 19681811150 DE19681811150 DE 19681811150 DE 1811150 A DE1811150 A DE 1811150A DE 1811150 A1 DE1811150 A1 DE 1811150A1
- Authority
- DE
- Germany
- Prior art keywords
- tetracycline
- preparation
- salts
- processes
- radical
- 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
- 239000004098 Tetracycline Substances 0.000 title claims description 9
- 235000019364 tetracycline Nutrition 0.000 title claims description 9
- 150000003522 tetracyclines Chemical class 0.000 title claims description 9
- 229960002180 tetracycline Drugs 0.000 title claims description 8
- 229930101283 tetracycline Natural products 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 title 1
- 229940052761 dopaminergic adamantane derivative Drugs 0.000 title 1
- 238000006683 Mannich reaction Methods 0.000 claims description 2
- 229960003805 amantadine Drugs 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- DVWJFTGEISXVSH-CWVFEVJCSA-N (1R,3S,5S,7Z,11R,12S,13Z,15Z,17Z,19Z,21R,23S,24R,25S)-21-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-12-ethyl-1,3,5,25-tetrahydroxy-11-methyl-9-oxo-10,27-dioxabicyclo[21.3.1]heptacosa-7,13,15,17,19-pentaene-24-carboxylic acid Chemical compound CC[C@H]1\C=C/C=C\C=C/C=C\[C@@H](C[C@@H]2O[C@@](O)(C[C@H](O)[C@H]2C(O)=O)C[C@@H](O)C[C@@H](O)C\C=C/C(=O)O[C@@H]1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](N)[C@@H]1O DVWJFTGEISXVSH-CWVFEVJCSA-N 0.000 description 1
- RMVMLZHPWMTQGK-SOUFLCLCSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1([C@H]2O)=CC=CC(O)=C1C(O)=C1[C@@H]2C[C@H]2[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]2(O)C1=O RMVMLZHPWMTQGK-SOUFLCLCSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- 241000283725 Bos Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241001400033 Omia Species 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- JCSGAUKCDAVARS-UHFFFAOYSA-N demethyltetracycline Natural products CN(C1C(=C(C(C2(C(=C3C(C4=C(C=CC=C4C(C3CC12)O)O)=O)O)O)=O)C(=O)N)O)C JCSGAUKCDAVARS-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- -1 propyl butyl Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 229930183279 tetramycin Natural products 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/127—Antibiotics
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Mycology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR143417 | 1968-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1811150A1 true DE1811150A1 (de) | 1969-12-11 |
Family
ID=8647339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681811150 Pending DE1811150A1 (de) | 1968-03-12 | 1968-11-27 | Tetracyclin- und Adamantan-Derivate und Verfahren zu ihrer Herstellung |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE722418A (is") |
| DE (1) | DE1811150A1 (is") |
| FR (1) | FR1604549A (is") |
| GB (1) | GB1204828A (is") |
| NL (1) | NL6815802A (is") |
-
1968
- 1968-03-12 FR FR143417A patent/FR1604549A/fr not_active Expired
- 1968-10-16 BE BE722418D patent/BE722418A/xx unknown
- 1968-11-06 NL NL6815802A patent/NL6815802A/xx unknown
- 1968-11-27 DE DE19681811150 patent/DE1811150A1/de active Pending
- 1968-12-12 GB GB59206/68A patent/GB1204828A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6815802A (is") | 1969-09-16 |
| FR1604549A (is") | 1971-11-29 |
| GB1204828A (en) | 1970-09-09 |
| BE722418A (is") | 1969-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2760005C2 (de) | Optisch aktive Norpinene und Verfahren zu ihrer Herstellung | |
| DE2710805A1 (de) | Titanchelat und verfahren zu seiner herstellung | |
| DE1927337B2 (de) | Verfahren zur Herstellung Schiffscher Basen des 2-Formyl-chinoxalin l,4dioxids | |
| DE69412598T2 (de) | Formylierungsverfahren für aromatische aldehyde | |
| DE2622638C2 (de) | Rifamycin-Verbindungen | |
| DE1695375C3 (de) | 25-Desacetyl-rifamycin-SV-derivate u. Verfahren zu ihrer Herstellung | |
| DE1811150A1 (de) | Tetracyclin- und Adamantan-Derivate und Verfahren zu ihrer Herstellung | |
| DE3715447A1 (de) | Verfahren fuer eine standardmischung von 0-( ss-hydroaethyl)-diosminen | |
| DE2134085C3 (de) | Spiramycin-hydrazone | |
| CH417630A (de) | Verfahren zur Herstellung von neuen cyclischen 2,3-O-Acetalen und 2,3-O-Ketalen von Butantetrolestern | |
| DE671167C (de) | Verfahren zur Herstellung von Kondensationsprodukten | |
| DE2232797B2 (de) | Halogenierte dibenzylphenole mit antibakterieller wirksamkeit, verfahren zu deren herstellung und antimikrobielle mittel | |
| DE1670378A1 (de) | Verfahren zur Herstellung einer Verbindung aus Phenylbutazon und ss-Diaethylaminoaethylamid der p-Chlorphenoxyessigsaeure | |
| DE2112778B2 (de) | Verfahren zur Herstellung von 2-CyBn-S^Ae-IeITaChIOr- bzw. brombenzoesäurealkylestern | |
| DE1643784C (de) | Biologisch wirksame Isothiocyanate und Verfahren zu deren Herstellung | |
| DE3525385A1 (de) | Verfahren zur herstellung von 2,2,6,6-tetramethyl-4-oxopiperidin | |
| DE703897C (de) | Verfahren zur Herstellung von basischem Methylquecksilbernitrat | |
| AT208000B (de) | Verfahren zur Herstellung antibakteriell wirksamer Verbindungen | |
| AT330162B (de) | Verfahren zur herstellung von substituierten 1,1-diphenyl-2-nitropropanen und -butanen | |
| DE2422430A1 (de) | Derivate der secalonsaeure d, verfahren zu ihrer herstellung und arzneimittel | |
| AT288413B (de) | Verfahren zur Herstellung neuer basischer Xanthonderivate und ihrer Salze | |
| AT236966B (de) | Verfahren zur Herstellung von neuen aliphatisch-heterocyclischen quaternären Ammoniumverbindungen | |
| DE737543C (de) | Weichmacher | |
| AT134999B (is") | ||
| DE876242C (de) | Verfahren zur Herstellung von Cyclopentanopolyhydrophenanthrenverbindungen mit Nebennierenrindenhormonwirkung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |