ZA200604945B - 18-membered nitrobenzyl-substituted and aminobenzyl-substituted cyclohexadepsipeptides for controlling endoparasites, and method for the production thereof - Google Patents
18-membered nitrobenzyl-substituted and aminobenzyl-substituted cyclohexadepsipeptides for controlling endoparasites, and method for the production thereof Download PDFInfo
- Publication number
- ZA200604945B ZA200604945B ZA200604945A ZA200604945A ZA200604945B ZA 200604945 B ZA200604945 B ZA 200604945B ZA 200604945 A ZA200604945 A ZA 200604945A ZA 200604945 A ZA200604945 A ZA 200604945A ZA 200604945 B ZA200604945 B ZA 200604945B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- alkyl
- salts
- general formula
- lactyl
- Prior art date
Links
- 244000079386 endoparasite Species 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 108010002156 Depsipeptides Proteins 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 230000003287 optical effect Effects 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 125000006502 nitrobenzyl group Chemical group 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000005864 Sulphur Substances 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- -1 methoxyethyl Chemical group 0.000 claims description 22
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000000802 nitrating effect Effects 0.000 claims description 4
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 150000001413 amino acids Chemical class 0.000 description 7
- 125000006413 ring segment Chemical group 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001663 caesium Chemical class 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 229910052751 metal Chemical class 0.000 description 2
- 239000002184 metal Chemical class 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 208000035657 Abasia Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical class N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 150000002306 glutamic acid derivatives Chemical class 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10359798A DE10359798A1 (de) | 2003-12-19 | 2003-12-19 | Cyclohexadepsipeptide zur Bekämpfung von Endoparasiten und ein Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200604945B true ZA200604945B (en) | 2007-09-26 |
Family
ID=34683580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200604945A ZA200604945B (en) | 2003-12-19 | 2006-06-15 | 18-membered nitrobenzyl-substituted and aminobenzyl-substituted cyclohexadepsipeptides for controlling endoparasites, and method for the production thereof |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7645738B2 (ja) |
| EP (1) | EP1715883B1 (ja) |
| JP (1) | JP5196788B2 (ja) |
| AT (1) | ATE429239T1 (ja) |
| AU (1) | AU2004308593B2 (ja) |
| BR (1) | BRPI0417828A (ja) |
| CA (1) | CA2550344A1 (ja) |
| DE (2) | DE10359798A1 (ja) |
| ES (1) | ES2323531T3 (ja) |
| MX (1) | MXPA06006662A (ja) |
| NZ (1) | NZ547999A (ja) |
| WO (1) | WO2005063277A1 (ja) |
| ZA (1) | ZA200604945B (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009012423A1 (de) * | 2009-03-10 | 2010-09-16 | Bayer Animal Health Gmbh | Zubereitung auf Ölbasis |
| WO2012028556A1 (en) * | 2010-08-31 | 2012-03-08 | Bayer Animal Health Gmbh | Macrocyclic lactones and their use and their combinations with other active substances |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4400464A1 (de) * | 1994-01-11 | 1995-07-13 | Bayer Ag | Endoparasitizide Mittel |
| DE4401389A1 (de) | 1994-01-19 | 1995-07-20 | Bayer Ag | Verwendung von cyclischen Depsipeptiden mit 12 Ringatomen zur Bekämpfung von Endoparasiten, neue cyclische Depsipeptide mit 12 Ringatomen und Verfahren zu ihrer Herstellung |
| DE4406025A1 (de) * | 1994-02-24 | 1995-08-31 | Bayer Ag | Milchsäure-haltige cyclische Depsipeptide mit 18 Ringatomen als endoparasitizide Mittel und Verfahren zu ihrer Herstellung |
| DE4412492A1 (de) | 1994-04-12 | 1995-10-19 | Bayer Ag | Verwendung von cyclischen Depsipeptiden mit 18 Ringatomen |
| DE19520275A1 (de) * | 1995-06-02 | 1996-12-05 | Bayer Ag | Endoparasitizide Mittel |
| CN1076349C (zh) * | 1997-06-04 | 2001-12-19 | 拜尔公司 | 去氧环缩肽及其防治体内寄生虫的用途 |
-
2003
- 2003-12-19 DE DE10359798A patent/DE10359798A1/de not_active Withdrawn
-
2004
- 2004-12-07 ES ES04803585T patent/ES2323531T3/es active Active
- 2004-12-07 AU AU2004308593A patent/AU2004308593B2/en not_active Ceased
- 2004-12-07 EP EP04803585A patent/EP1715883B1/de not_active Not-in-force
- 2004-12-07 DE DE502004009401T patent/DE502004009401D1/de active Active
- 2004-12-07 AT AT04803585T patent/ATE429239T1/de not_active IP Right Cessation
- 2004-12-07 BR BRPI0417828-9A patent/BRPI0417828A/pt not_active Application Discontinuation
- 2004-12-07 JP JP2006544278A patent/JP5196788B2/ja not_active Expired - Fee Related
- 2004-12-07 WO PCT/EP2004/013896 patent/WO2005063277A1/de active Application Filing
- 2004-12-07 MX MXPA06006662A patent/MXPA06006662A/es active IP Right Grant
- 2004-12-07 NZ NZ547999A patent/NZ547999A/en not_active IP Right Cessation
- 2004-12-07 US US10/582,555 patent/US7645738B2/en not_active Expired - Fee Related
- 2004-12-07 CA CA002550344A patent/CA2550344A1/en not_active Abandoned
-
2006
- 2006-06-15 ZA ZA200604945A patent/ZA200604945B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007514671A (ja) | 2007-06-07 |
| NZ547999A (en) | 2010-07-30 |
| WO2005063277A1 (de) | 2005-07-14 |
| US20080026990A1 (en) | 2008-01-31 |
| MXPA06006662A (es) | 2006-08-31 |
| BRPI0417828A (pt) | 2007-04-10 |
| DE502004009401D1 (de) | 2009-06-04 |
| AU2004308593A1 (en) | 2005-07-14 |
| EP1715883A1 (de) | 2006-11-02 |
| ATE429239T1 (de) | 2009-05-15 |
| AU2004308593B2 (en) | 2011-11-10 |
| US7645738B2 (en) | 2010-01-12 |
| ES2323531T3 (es) | 2009-07-20 |
| JP5196788B2 (ja) | 2013-05-15 |
| EP1715883B1 (de) | 2009-04-22 |
| DE10359798A1 (de) | 2005-07-21 |
| CA2550344A1 (en) | 2005-07-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IL176247A0 (en) | Cyclopropane compounds and pharmaceutical use thereof | |
| CA2155104A1 (en) | Heterocyclic-substituted alkyl amide acat inhibitors | |
| IE883845L (en) | Adenosine derivative | |
| LU90317I2 (fr) | Tacrolimus et ses sels et dérivés pharmaceutiquement acceptables | |
| GB0129476D0 (en) | Organic compounds | |
| AU1714801A (en) | Substituted isoxazolines and their use as antibacterial agents | |
| YU52403A (sh) | Heterociklična jedinjenja koja imaju antibakterijsko dejstvo, postupak za njihovo dobijanje i farmaceutske smeše koje ih sadrže | |
| ATE264268T1 (de) | Verfahren zur herstellung von zsm-5 und zsm-11 | |
| MX9700871A (es) | Procedimiento para hacer compuestos antimicrobianos. | |
| RS20050450A (en) | 2-aminocarbonyl-quinoline compounds as platelet adenosine diphosphate receptor antagonists | |
| AU6471200A (en) | Substituted aromatic-ring compounds, process for producing the same, and use | |
| ZA200604945B (en) | 18-membered nitrobenzyl-substituted and aminobenzyl-substituted cyclohexadepsipeptides for controlling endoparasites, and method for the production thereof | |
| MXPA04008926A (es) | Inhibidores de entrada a moleculas pequenas. | |
| ATE375343T1 (de) | Neue beta-lactamverbindungen und verfahren zu deren herstellung | |
| AU1076802A (en) | Selective glucocorticoid receptor agonists | |
| EA200000929A2 (ru) | Новые цианоиндольные соединения-ингибиторы повторного захвата серотонина, способ их получения и содержащие их фармацевтические композиции | |
| MXPA04003086A (es) | Proceso para sintesis estereoselectiva de 2-hidroximetil-cromanos. | |
| MX9605713A (es) | Procedimiento para preparar un derivado de acetoxiazetidinona e intermedio del mismo. | |
| PL324197A1 (en) | Derivatives of hydroxylamine and pharmaceutic agents against ischaemia | |
| HU902079D0 (en) | Process for producing glutaric acid derivatives and pharmaceutical preparatives containing such compounds | |
| AU7032594A (en) | Azoxycyanobenzene derivatives | |
| Thomas et al. | Synthesis of 9β-methyl-2-alkyl-7-oxo-5-arylmorphans | |
| ATE134379T1 (de) | 38-decarboxy-38-hydroxymethylderivate von teicoplaninantibiotika, und verfahren zu deren herstellung | |
| HUP0003321A2 (hu) | Eljárás 2-alkiltiobenzonitril-származékok előállítására | |
| AU5196299A (en) | N-cyclopropyl-2-difluoromethoxy-3-halogenoanilines and intermediates for the preparation thereof |