GB921252A - New tetracycline derivatives - Google Patents
New tetracycline derivativesInfo
- Publication number
- GB921252A GB921252A GB8743/61A GB874361A GB921252A GB 921252 A GB921252 A GB 921252A GB 8743/61 A GB8743/61 A GB 8743/61A GB 874361 A GB874361 A GB 874361A GB 921252 A GB921252 A GB 921252A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetracycline
- amides
- hydrogen
- amino acid
- alkyl
- 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
- 239000004098 Tetracycline Substances 0.000 title abstract 4
- 229960002180 tetracycline Drugs 0.000 title abstract 4
- 235000019364 tetracycline Nutrition 0.000 title abstract 4
- 229930101283 tetracycline Natural products 0.000 title abstract 4
- 150000003522 tetracyclines Chemical class 0.000 title abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 150000001408 amides Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 abstract 2
- 239000004471 Glycine Substances 0.000 abstract 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 abstract 2
- 239000004472 Lysine Substances 0.000 abstract 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract 2
- 235000004279 alanine Nutrition 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 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 abstract 1
- GUXHBMASAHGULD-SEYHBJAFSA-N (4s,4as,5as,6s,12ar)-7-chloro-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)=C(Cl)C=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 GUXHBMASAHGULD-SEYHBJAFSA-N 0.000 abstract 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004099 Chlortetracycline Substances 0.000 abstract 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 1
- 239000004100 Oxytetracycline Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 abstract 1
- 235000001014 amino acid Nutrition 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 abstract 1
- 229960004475 chlortetracycline Drugs 0.000 abstract 1
- CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 abstract 1
- 235000019365 chlortetracycline Nutrition 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 229960002398 demeclocycline Drugs 0.000 abstract 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 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960000625 oxytetracycline Drugs 0.000 abstract 1
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 abstract 1
- 235000019366 oxytetracycline Nutrition 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000002504 physiological saline solution Substances 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003254 radicals Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
- C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
- C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to water-soluble tetracycline derivatives of the formula: -T-CH2-NH-CH(R)-CONR1R2 where T is a radical derived from tetracycline, oxytetracycline, chlortetracycline, demethyl tetracycline or demethyl chlortetracycline by removal of a hydrogen atom and R is hydrogen, alkyl, or substituted alkyl such that the compound RCH(NH2)COOH is a known, naturally occurring amino acid and R1 and R2 may be the same or different and represent hydrogen, alkyl, hydroxyalkyl, aminoalkyl, alkylaminoalkyl or dialkylaminoalkyl or R1 is hydrogen and R2 is amino, which are obtainable by the condensation of a said tetracycline with formaldehyde e.g. as formalin or trioxane and an amide of an a -amino acid of the formula:-R-CH(NH2)-CONR1R2 where R, R1 and R2 are as before. Preferably R is such that RCH(NH2)COOH is glycine, alanine, serine or lysine. Preferred a -amino acid amides are the unsubstituted amides, the N-(b -hydroxyethyl)- and N,N-di(b -hydroxyethyl)amides and the N or N,N mono or dimethyl or ethyl amides of glycine, alanine, serine or lysine. The above compounds may be formulated as pharmaceutical compositions preferably for oral or parenteral administration in association with a pharmaceutical carrier. The compositions may be prepared as tablets, pills or powders which may be encapsulated or the active ingredients may be incorporated in a syrup base or dissolved in water or physiological saline and filled into ampoules.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT406560 | 1960-03-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB921252A true GB921252A (en) | 1963-03-20 |
Family
ID=11112045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8743/61A Expired GB921252A (en) | 1960-03-09 | 1961-03-09 | New tetracycline derivatives |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1003M (en) |
| GB (1) | GB921252A (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004502752A (en) * | 2000-07-07 | 2004-01-29 | トラスティーズ・オブ・タフツ・カレッジ | 9-substituted minocycline compounds |
| WO2003075857A3 (en) * | 2002-03-08 | 2004-02-05 | Paratek Pharm Innc | Amino-methyl substituted tetracycline compounds |
| US7208482B2 (en) | 2001-03-13 | 2007-04-24 | Paratek Pharmaceuticals, Inc. | 9-aminoacyl tetracycline compounds and methods of use thereof |
| US7323492B2 (en) | 2001-08-02 | 2008-01-29 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl 9-aminoacyl tetracycline compounds and methods of use thereof |
| US7521437B2 (en) | 2000-06-16 | 2009-04-21 | Trustees Of Tufts College | 7-phenyl-substituted tetracycline compounds |
| US7553828B2 (en) | 2001-03-13 | 2009-06-30 | Paratek Pharmaceuticals, Inc. | 9-aminomethyl substituted minocycline compounds |
| US7612053B2 (en) | 2000-05-15 | 2009-11-03 | Paratek Pharmaceuticals, Inc. | 7-Substituted fused ring tetracycline compounds |
| US7696187B2 (en) | 1999-09-14 | 2010-04-13 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| US7696358B2 (en) | 2001-03-13 | 2010-04-13 | Paratek Pharmaceuticals, Inc. | Five-membered heterocyclyl tetracycline compounds and methods of use thereof |
| US7696186B2 (en) | 2001-03-13 | 2010-04-13 | Paratek Pharmaceuticals, Inc. | 7,9-substituted tetracycline compounds |
| US7820641B2 (en) | 2002-03-21 | 2010-10-26 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US8106225B2 (en) * | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| US8318706B2 (en) | 2006-12-21 | 2012-11-27 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US8513223B2 (en) | 2006-12-21 | 2013-08-20 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for treatment of inflammatory skin disorders |
| US8518912B2 (en) | 2007-11-29 | 2013-08-27 | Actelion Pharmaceuticals Ltd. | Phosphonic acid derivates and their use as P2Y12 receptor antagonists |
| US9533943B2 (en) | 2003-07-09 | 2017-01-03 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
-
1961
- 1961-03-09 FR FR855094A patent/FR1003M/en active Active
- 1961-03-09 GB GB8743/61A patent/GB921252A/en not_active Expired
Cited By (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8106225B2 (en) * | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| US7696187B2 (en) | 1999-09-14 | 2010-04-13 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| US7612053B2 (en) | 2000-05-15 | 2009-11-03 | Paratek Pharmaceuticals, Inc. | 7-Substituted fused ring tetracycline compounds |
| US8288570B2 (en) | 2000-05-15 | 2012-10-16 | Paratek Pharmaceuticals, Inc. | 7-iodo tetracyclines and related methods |
| US7893282B2 (en) | 2000-05-15 | 2011-02-22 | Paratek Pharmaceuticals, Inc. | 7-substituted fused ring tetracycline compounds |
| US8168810B2 (en) | 2000-06-16 | 2012-05-01 | Trustees Of Tufts College | 7-phenyl-substituted tetracycline compounds |
| US7851460B2 (en) | 2000-06-16 | 2010-12-14 | Trustees Of Tufts College | 7-phenyl-substituted tetracycline compounds |
| US7521437B2 (en) | 2000-06-16 | 2009-04-21 | Trustees Of Tufts College | 7-phenyl-substituted tetracycline compounds |
| US8258120B2 (en) | 2000-07-07 | 2012-09-04 | Paratek Pharmaceuticals, Inc. | 9-substituted minocycline compounds |
| JP2009029785A (en) * | 2000-07-07 | 2009-02-12 | Tufts College | 9-Substituted minocycline compounds |
| US9090541B2 (en) | 2000-07-07 | 2015-07-28 | Paratek Pharmaceuticals, Inc. | 9-substituted minocycline compounds |
| US8048867B2 (en) | 2000-07-07 | 2011-11-01 | Trustees Of Tufts College | 9-substituted minocycline compounds |
| JP2004502752A (en) * | 2000-07-07 | 2004-01-29 | トラスティーズ・オブ・タフツ・カレッジ | 9-substituted minocycline compounds |
| US7553828B2 (en) | 2001-03-13 | 2009-06-30 | Paratek Pharmaceuticals, Inc. | 9-aminomethyl substituted minocycline compounds |
| US8304445B2 (en) | 2001-03-13 | 2012-11-06 | Paratek Pharmaceuticals, Inc. | 7-pyrazolyl tetracycline compounds and methods of use thereof |
| US7208482B2 (en) | 2001-03-13 | 2007-04-24 | Paratek Pharmaceuticals, Inc. | 9-aminoacyl tetracycline compounds and methods of use thereof |
| US7696186B2 (en) | 2001-03-13 | 2010-04-13 | Paratek Pharmaceuticals, Inc. | 7,9-substituted tetracycline compounds |
| US7696358B2 (en) | 2001-03-13 | 2010-04-13 | Paratek Pharmaceuticals, Inc. | Five-membered heterocyclyl tetracycline compounds and methods of use thereof |
| US7897784B2 (en) | 2001-03-13 | 2011-03-01 | Paratek Pharmaceuticals, Inc. | Process for preparing five-membered heterocyclyl tetracycline compounds and methods of use thereof |
| US9365500B2 (en) | 2001-03-13 | 2016-06-14 | Paratek Pharmaceuticals, Inc. | 9-aminomethyl substituted minocycline compounds |
| US8101591B2 (en) | 2001-03-13 | 2012-01-24 | Paratek Pharmaceuticals, Inc. | 9-aminoacyl tetracycline compounds and methods of use thereof |
| US7652002B2 (en) | 2001-03-13 | 2010-01-26 | Paratek Pharmaceuticals, Inc. | 9-aminoacyl tetracycline compounds and methods of use thereof |
| US7323492B2 (en) | 2001-08-02 | 2008-01-29 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl 9-aminoacyl tetracycline compounds and methods of use thereof |
| US8211937B2 (en) | 2001-08-02 | 2012-07-03 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl 9-aminoacyl tetracycline compounds and methods of use thereof |
| US7326696B2 (en) | 2002-03-08 | 2008-02-05 | Paratek Pharmaceuticals, Inc. | Amino-methyl substituted tetracycline compounds |
| WO2003075857A3 (en) * | 2002-03-08 | 2004-02-05 | Paratek Pharm Innc | Amino-methyl substituted tetracycline compounds |
| EA013819B1 (en) * | 2002-03-08 | 2010-08-30 | Паратек Фармасьютикалс, Инк. | Amino-methyl substituted tetracycline compounds |
| AU2003220123B2 (en) * | 2002-03-08 | 2009-05-07 | Paratek Pharmaceuticals, Inc. | Amino-methyl substituted tetracycline compounds |
| US7820641B2 (en) | 2002-03-21 | 2010-10-26 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US9533943B2 (en) | 2003-07-09 | 2017-01-03 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US9012433B2 (en) | 2006-12-21 | 2015-04-21 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US8513223B2 (en) | 2006-12-21 | 2013-08-20 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for treatment of inflammatory skin disorders |
| US8318706B2 (en) | 2006-12-21 | 2012-11-27 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US9481639B2 (en) | 2006-12-21 | 2016-11-01 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for treatment of inflammatory skin disorders |
| US8518912B2 (en) | 2007-11-29 | 2013-08-27 | Actelion Pharmaceuticals Ltd. | Phosphonic acid derivates and their use as P2Y12 receptor antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1003M (en) | 1961-12-18 |
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