NZ537212A - Antibacterial amide macrocycles - Google Patents
Antibacterial amide macrocyclesInfo
- Publication number
- NZ537212A NZ537212A NZ537212A NZ53721203A NZ537212A NZ 537212 A NZ537212 A NZ 537212A NZ 537212 A NZ537212 A NZ 537212A NZ 53721203 A NZ53721203 A NZ 53721203A NZ 537212 A NZ537212 A NZ 537212A
- Authority
- NZ
- New Zealand
- Prior art keywords
- hydrogen
- alkyl
- substituents
- compound
- cycloalkyl
- Prior art date
Links
- -1 amide macrocycles Chemical class 0.000 title claims abstract 31
- 230000000844 anti-bacterial effect Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract 7
- 239000003814 drug Substances 0.000 claims abstract 5
- 238000004519 manufacturing process Methods 0.000 claims abstract 5
- 238000011321 prophylaxis Methods 0.000 claims abstract 4
- 238000011282 treatment Methods 0.000 claims abstract 4
- 208000035143 Bacterial infection Diseases 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 48
- 239000001257 hydrogen Substances 0.000 claims 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 46
- 125000001424 substituent group Chemical group 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 17
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 125000003282 alkyl amino group Chemical group 0.000 claims 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 8
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 150000001413 amino acids Chemical class 0.000 claims 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 4
- 125000000539 amino acid group Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 2
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 2
- 235000019359 magnesium stearate Nutrition 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 229920002261 Corn starch Polymers 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
- 229920002472 Starch Polymers 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 1
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 230000006835 compression Effects 0.000 claims 1
- 238000007906 compression Methods 0.000 claims 1
- 239000008120 corn starch Substances 0.000 claims 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 229940100692 oral suspension Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- 235000019698 starch Nutrition 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 230000008961 swelling Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 229920001285 xanthan gum Polymers 0.000 claims 1
- 229940082509 xanthan gum Drugs 0.000 claims 1
- 235000010493 xanthan gum Nutrition 0.000 claims 1
- 239000000230 xanthan gum Substances 0.000 claims 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Disclosed are amide macrocycles of formula (I), compositions comprising them and methods for their production. The compositions are used for the manufacture of medicaments for the treatment and/or prophylaxis of bacterial diseases.
Description
New Zealand Paient Spedficaiion for Paient Number 537212 / '■ '
Claims (25)
1. A compound of the formula in which R1 is hydrogen, alkyl, aryl, heteroaryl, heterocyclyl, alkylcarbonyl, arylcarbonyl, heterocyclylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl, arylsulfonyl, heterocyclylsulfonyl, heteroarylsulfonyl or a carbonyl-linked amino acid residue, where R1 apart from hydrogen may be substituted by 0, 1, 2 or 3 substituents R1'1, where the substituents R1"1 are selected independently of one another from the group consisting of halogen, alkyl, trifluoromethyl, trifluoromethoxy, nitro, cyano, amino, alkylamino, dialkylamino, cycloalkyl, aryl, heteroaryl, heterocyclyl, hydroxy, alkoxy and carboxyl, >y R is hydrogen or alkyl, where R2 apart from hydrogen may be substituted by 0, 1, 2 or 3 substituents R2'1, where the substituents R2"1 are selected Le A 35722CPCT) - 167- independently of one another from the group consisting of halogen, amino, alkylamino and dialkylamino, R1 and R2 together with the nitrogen atom to which they are bonded form a heterocycle which may be substituted by 0, 1 or 2 substituents R1'2, where the substituents R1"2 are selected independently of one another from the group consisting of halogen, trifluoromethyl, amino, alkylamino, dialkylamino, cycloalkyl, aryl, heteroaryl, heterocyclyl, hydroxy, alkoxy, carboxyl, alkoxycarbonyl and aminocarbonyl, R3 is hydrogen, alkyl or the side group of an amino acid, in which alkyl may be substituted by 0, 1, 2 or 3 substituents R3"1, where the substituents R3"1 are selected independently of one another from the group consisting of trifluoromethyl, nitro, amino, alkylamino, dialkylamino, cycloalkyl, aryl, heteroaryl, heterocyclyl, hydroxy, alkoxy, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, guanidino and amidino, in which cycloalkyl, aryl, heteroaryl and heterocyclyl may be substituted by 0, 1 or 2 substituents R3"2, where the substituents R3"2 are selected independently of one another from the group consisting of halogen, alkyl, trifluoromethyl and amino, and in which free amino groups in the side group of the amino acid may be substituted by alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylaminocarbonyl, alkylsulfonyl, arylsulfonyl, heterocyclylsulfonyl or heteroarylsulfonyl, Le A 35722(PCD -168- R3 is hydrogen, Ci-C6-alkyl or C3-Cg-cycloalkyl, R4 is hydrogen, Ci-C6-alkyl or Cs-Cg-cycloalkyl, R5 is hydrogen, alkyl, alkenyl, cycloalkyl, aryl, heteroaryl, heterocyclyl or an amine-linked amino acid residue, where R5 may be substituted by 0, 1, 2 or 3 substituents R5"1, where the substituents R5"1 are selected independently of one another from the group consisting of halogen, alkyl, trifluoromethyl, trifluoromethoxy, nitro, cyano, amino, alkylamino, dialkylamino, cycloalkyl, aryl, heteroaryl, heterocyclyl, hydroxy, alkoxy, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, heterocyclylaminosulfonyl, heteroarylaminosulfonyl, aminocarbonylamino, hydroxycarbonylamino and alkoxycarbonylamino, in which alkyl, alkylamino, dialkylamino, cycloalkyl, aryl, heteroaryl and heterocyclyl may be substituted by 0, 1, 2 or 3 substituents R5"2, c where the substituents R " are selected independently of one another from the group consisting of hydroxy, amino, carboxyl and aminocarbonyl, R6 is hydrogen, alkyl or cycloalkyl, or R5 and R6 together with the nitrogen atom to which they are bonded form a heterocycle which may be substituted by 0, 1, 2 or 3 substituents R5"6, where the substituents R5"6 are selected independently of one another from the group consisting of halogen, alkyl, trifluoromethyl, nitro, amino, alkylamino, dialkylamino, cycloalkyl, aryl, halogenated aryl, Le A 35722(TCT) -169 - heteroaryl, heterocyclyl, hydroxy, alkoxy, carboxyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl and dialkylaminocarbonyl, R7 is hydrogen, Ci-C6-alkyl, alkylcarbonyl or C3-Cg-cycloalkyl, R8 is hydrogen or Ci-C6-alkyl, and R9 is hydrogen or Ci-C6-alkyl, and one of the salts thereof, or one of the solvates thereof and one of the solvates of the salts thereof.
2. A compound as claimed in claim 1, characterized in that it corresponds to the formula R1R2 NR5R6 (0 in which R1 to R9 have the same meaning as in formula (I).
3. A compound as claimed in claim 1 or 2, characterized in that R is hydrogen, alkyl or alkylcarbonyl, R2 is hydrogen, Le A 35722CPCT) -170 - R3 is alkyl or the side group of an amino acid, in which alkyl may be substituted by 0,1,2 or 3 substituents R3"1, where the substituents R3'1 are selected independently of one another from the group consisting of trifluoromethyl, nitro, amino, alkylamino, dialkylamino, cycloalkyl, aryl, heteroaryl, heterocyclyl, hydroxy, alkoxy, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, guanidino and amidino, in which cycloalkyl, aryl, heteroaryl and heterocyclyl may be substituted by 0, 1 or 2 substituents R3"2, where the substituents R3'2 are selected independently of one another from the group consisting of halogen, alkyl, trifluoromethyl and amino, and in which free amino groups in the side group of the amino acid may be substituted by alkyl, R3 is hydrogen, Ci-C6-alkyl or Cs-Cg-cycloalkyl, R4 is hydrogen, Ci-C6-alkyl or C3-Cg-cycloalkyl, R5 is hydrogen, alkyl, alkenyl, cycloalkyl, aryl, heteroaryl, heterocyclyl or an amine-linked amino acid residue, where alkyl, alkenyl, cycloalkyl, aryl, heteroaryl and heterocyclyl may be substituted by 0, 1, 2 or 3 substituents R5"1, where the substituents R5"1 are selected independently of one another from the group consisting of halogen, alkyl, trifluoromethyl, trifluoromethoxy, nitro, cyano, amino, alkylamino, dialkylamino, cycloalkyl, aryl, heteroaryl, heterocyclyl, hydroxy, alkoxy, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl and dialkylaminocarbonyl, in which alkyl, alkylamino, dialkylamino, cycloalkyl, aryl, heteroaryl r 'y and heterocyclyl may be substituted by 0, 1, 2 or 3 substituents R ', -171 - where the substituents R5'2 are selected independently of one another from the group consisting of hydroxy, amino, carboxyl and aminocarbonyl, R6 is hydrogen, alkyl or cycloalkyl, R5 and R6 together with the nitrogen atom to which they are bonded form a heterocycle which may be substituted by 0, 1,2 or 3 substituents R5"6, where the substituents R5*6 are selected independently of one another from the group consisting of halogen, alkyl, amino, alkylamino, dialkylamino, hydroxy, alkoxy, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl and dialkylaminocarbonyl, R7 is hydrogen, Ci-C6-alkyl, alkylcarbonyl or C3-Cg-cycloalkyl, R8 is hydrogen, and R9 is hydrogen.
4.A compound as claimed in any one of claims 1 to 3, characterized in that R1 is hydrogen, R2 is hydrogen, R3 is aminocarbonylmethyl, 3-aminoprop-l-yl, 2-hydroxy-3-aminoprop-1-yl, l-hydroxy-3-aminoprop-l-yl, 3-guanidinoprop-l-yl, 2-aminocarbonylethyl, 2-hydroxycarbonylethyl, 4-aminobut-l-yl, Intellectual Property Office of N.Z. - 2 AUG 2005 RECEIVED Le A 35722CPCD - 172 - hydroxymethyl, 2-hydroxyethyl, 2-aminoethyl, 4-amino-3-hydroxybut-l-yl or (l-piperidin-3-yl)methyl, R3' is hydrogen, R4 is hydrogen, methyl, ethyl, isopropyl or cyclopropyl, R5 is hydrogen, Ci-C6-alkyl or C3-Cg-cycloalkyl, where alkyl and cycloalkyl may be substituted by 0, 1, 2 or 3 substituents R5"1, where the substituents R5'1 are selected independently of one another from the group consisting of halogen, Ci-C6-alkyl, trifluoromethyl, trifluoromethoxy, amino, C1-C6-alkylamino, Ci-C6-dialkylamino, C3-Cg-cycloalkyl, C6-Cio-aryl, 5- to 10-membered heteroaryl, 5- to 7-membered heterocyclyl, hydroxy, alkoxy, carboxyl, Ci-C6-alkoxycarbonyl, aminocarbonyl, C1-C6-alkylaminocarbonyl and Ci-C6-dialkylaminocarbonyl, R6 is hydrogen or methyl, R5 and R6 together with the nitrogen atom to which they are bonded form a piperidinyl or morpholinyl, R7 is hydrogen, R8 is hydrogen, R9 is hydrogen. -173-
5.A compound as claimed in any one of claims 1 to 4, characterized in that R1 is hydrogen, R is hydrogen, R3 is 3-aminoprop-l-yl or 2-hydroxy-3-aminoprop-l-yl, R3 is hydrogen, R4 is hydrogen or methyl, R5 is hydrogen, Ci-C6-alkyl or cyclopropyl, where alkyl may be substituted by 0, 1, 2 or 3 substituents R5"1, where the substituents R5"1 are selected independently of one another from the group consisting of trifluoromethyl, amino, hydroxy, carboxyl, aminocarbonyl and phenyl, R6 is hydrogen or methyl, R7 is hydrogen, R is hydrogen and R9 is hydrogen.
6.A compound as claimed in any one of claims 1 to 3, characterized in that R1 is hydrogen. Intellectual Property Office of M.Z. - 2 AUG 2005 RECEIVED -174 -
7. A compound as claimed in any one of claims 1,2 and 6, characterized in that R2 is hydrogen.
8. A compound as claimed in any one of claims 1 to 4,6 and 7, characterized in that 5 R3 is 3-aminoprop-l-yl or 2-hydroxy-3-aminoprop-l-yl.
9. A compound as claimed in any one of claims 1 to 3 or 6 to 8, characterized in that R3 is hydrogen.
10.10. A compound as claimed in any one of claims 1 to 4 or 6 to 9, characterized in that R4 is hydrogen or methyl.
11. A compound as claimed in any one of claims 1 to 4 or 6 to 10, characterized in that 15 R5 is hydrogen, Ci-C6-alkyl or cyclopropyl, where alkyl may be substituted by 0, 1, 2 or 3 substituents R5"1, where the substituents R5"1 are selected independently of one another from the group consisting of trifluoromethyl, amino, hydroxy, carboxyl, aminocarbonyl and 20 phenyl.
12. A compound as claimed in any one of claims 1 to 3 or 6 to 11, characterized in that R6 is hydrogen or methyl. 25
13. A compound as claimed in any one of claims 1 to 4 or 6 to 12, characterized in that R5 and R6 together with the nitrogen atom to which they are bonded form a piperidinyl or morpholinyl.
14. A compound as claimed in any one of claims 1 to 3 or 6 to 13, characterized in 30 that R7 is hydrogen.
15. A compound as claimed in any one of claims 1,2, 6 to 14, characterized in that R8 is hydrogen. Intellectual Property Offinft o< MX - 2 AUG 2005 RECEIVED -175-
16.A compound as claimed in any one of claims 1,2, 6 to 15, characterized in that R9 is hydrogen.
17.A process for preparing a compound of the formula (I) as claimed in claim 1, characterized in that a compound of the formula in which R1 to R4 and R7 to R9 have the meaning indicated in claim 1, is reacted with a compound of the formula H-NR5R6 (III), in which R5 and R6 have the meaning indicated in claim 1.
18.A compound as claimed in any one of claims 1 to 16 for the treatment and/or prophylaxis of diseases.
19.A medicament comprising at least one compound as claimed in any one of claims 1 to 16 in combination with at least one pharmaceutically suitable, pharmaceutically acceptable carrier or other excipients.
20.The use of a compound as claimed in any one of claims 1 to 16 for producing a medicament for the treatment and/or prophylaxis of bacterial diseases. Intellectual Property Office of N.Z. - 2 AUG 2005 RECEIVED -176- 5
21. A medicament as claimed in claim 19 for the treatment and/or prophylaxis of bacterial infections.
22. A compound according to claim 1, substantially as herein described or exemplified.
23. A process according to claim 17, substantially as herein described or exemplified.
24. A medicament according to claim 19, substantially as herein described or exemplified.
25. A use according to claim 20, substantially as herein described or exemplified.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE20226921 | 2002-06-17 | ||
| PCT/EP2003/006078 WO2003106480A1 (en) | 2002-06-17 | 2003-06-10 | Antibacterial amide macrocycles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ537212A true NZ537212A (en) | 2006-06-30 |
Family
ID=36604156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ537212A NZ537212A (en) | 2002-06-17 | 2003-06-10 | Antibacterial amide macrocycles |
Country Status (1)
| Country | Link |
|---|---|
| NZ (1) | NZ537212A (en) |
-
2003
- 2003-06-10 NZ NZ537212A patent/NZ537212A/en not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ASS | Change of ownership |
Owner name: AICURIS GMBH AND CO. KG, DE Free format text: OLD OWNER(S): BAYER HEALTHCARE AG |
|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |