JP2008534540A5 - - Google Patents
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- Publication number
- JP2008534540A5 JP2008534540A5 JP2008503408A JP2008503408A JP2008534540A5 JP 2008534540 A5 JP2008534540 A5 JP 2008534540A5 JP 2008503408 A JP2008503408 A JP 2008503408A JP 2008503408 A JP2008503408 A JP 2008503408A JP 2008534540 A5 JP2008534540 A5 JP 2008534540A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- independently
- represents hydrogen
- methyl
- hydrogen
- 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.)
- Withdrawn
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 116
- 239000001257 hydrogen Substances 0.000 claims description 116
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
- 150000002431 hydrogen Chemical class 0.000 claims description 47
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 43
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 13
- 125000004193 piperazinyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 208000035143 Bacterial infection Diseases 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 238000004517 catalytic hydrocracking Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 35
- 150000001721 carbon Chemical group 0.000 claims 21
- 239000003814 drug Substances 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 0 CCC(*)C(C)(C)C(C)(C)CCNC(*)=O Chemical compound CCC(*)C(C)(C)C(C)(C)CCNC(*)=O 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 206010039438 Salmonella Infections Diseases 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 206010039447 salmonellosis Diseases 0.000 description 4
- 201000004813 Bronchopneumonia Diseases 0.000 description 3
- 206010012735 Diarrhoea Diseases 0.000 description 3
- 208000004396 mastitis Diseases 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- -1 2- (Trimethylsilyl) ethyl Chemical group 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000204031 Mycoplasma Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 241000606860 Pasteurella Species 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000271566 Aves Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 206010048461 Genital infection Diseases 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- 206010033078 Otitis media Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 241000287531 Psittacidae Species 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 208000027515 Tracheal disease Diseases 0.000 description 1
- 206010046793 Uterine inflammation Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 208000029182 enterotoxemia Diseases 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 201000007094 prostatitis Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005014245A DE102005014245A1 (de) | 2005-03-30 | 2005-03-30 | Antibakterielle Amid-Makrozyklen V |
| PCT/EP2006/002617 WO2006103015A1 (de) | 2005-03-30 | 2006-03-22 | Antibakterielle amid-makrozyklen v |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008534540A JP2008534540A (ja) | 2008-08-28 |
| JP2008534540A5 true JP2008534540A5 (https=) | 2009-05-21 |
Family
ID=36572224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008503408A Withdrawn JP2008534540A (ja) | 2005-03-30 | 2006-03-22 | 抗菌性アミド−マクロサイクルｖ |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20080275018A1 (https=) |
| EP (1) | EP1869068A1 (https=) |
| JP (1) | JP2008534540A (https=) |
| KR (1) | KR20070116169A (https=) |
| CN (1) | CN101228182A (https=) |
| AU (1) | AU2006228751A1 (https=) |
| BR (1) | BRPI0612219A2 (https=) |
| CA (1) | CA2602755A1 (https=) |
| DE (1) | DE102005014245A1 (https=) |
| IL (1) | IL185899A0 (https=) |
| MX (1) | MX2007012146A (https=) |
| NO (1) | NO20075270L (https=) |
| NZ (1) | NZ562003A (https=) |
| RU (1) | RU2409588C2 (https=) |
| UA (1) | UA91541C2 (https=) |
| WO (1) | WO2006103015A1 (https=) |
| ZA (1) | ZA200709336B (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10358824A1 (de) | 2003-12-16 | 2005-07-21 | Bayer Healthcare Ag | Antibakterielle Makrozyklen mit substituiertem Biphenyl |
| DE102005032781A1 (de) * | 2005-07-14 | 2007-01-18 | Aicuris Gmbh & Co. Kg | Antibakterielle Amid-Markozyklen VII |
| US9187524B2 (en) | 2010-09-15 | 2015-11-17 | The Scripps Research Institute | Broad spectrum antibiotic arylomycin analogs |
| TWI642684B (zh) * | 2011-05-27 | 2018-12-01 | Ｒｑｘ製藥股份有限公司 | 廣效性抗生素 |
| US10501493B2 (en) | 2011-05-27 | 2019-12-10 | Rqx Pharmaceuticals, Inc. | Broad spectrum antibiotics |
| EA201590871A1 (ru) | 2012-11-21 | 2015-11-30 | АрКьюЭкс ФАРМАСЪЮТИКЛС, ИНК. | Макроциклические антибиотики широкого спектра действия |
| BR112016027232A2 (pt) | 2014-05-20 | 2018-06-26 | Genentech Inc | antibióticos macrocíclicos de amplo espectro |
| UA124303C2 (uk) | 2015-10-27 | 2021-08-25 | Ф. Хоффманн-Ля Рош Аг | Пептидні макроцикли проти acinetobacter baumannii |
| US11072635B2 (en) | 2015-11-20 | 2021-07-27 | Rqx Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| EP3388444A1 (en) * | 2017-04-10 | 2018-10-17 | F. Hoffmann-La Roche AG | Anti-bacterial peptide macrocycles and use thereof |
| EP3672939A1 (en) | 2017-08-21 | 2020-07-01 | Celgene Corporation | Processes for preparation of (s)-tert-butyl 4,5-diamino-5-oxopentanoate |
| US11505573B2 (en) | 2018-03-28 | 2022-11-22 | Hoffmann-La Roche Inc. | Peptide macrocycles against Acinetobacter baumannii |
| US11819532B2 (en) | 2018-04-23 | 2023-11-21 | Hoffmann-La Roche Inc. | Peptide macrocycles against Acinetobacter baumannii |
| ES2961566T3 (es) | 2019-05-28 | 2024-03-12 | Hoffmann La Roche | Antibióticos macrocíclicos de amplio espectro |
| WO2024262518A1 (ja) * | 2023-06-20 | 2024-12-26 | 国立大学法人北海道大学 | スキャニング用アミノ酸化合物、スキャニング用改変ペプチド、スキャニング用キット及びペプチドの活性部位のスキャニング方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3452136A (en) * | 1968-04-17 | 1969-06-24 | American Cyanamid Co | Antibiotic af283 and production thereof |
| FR2720066B1 (fr) * | 1994-05-20 | 1996-06-28 | Rhone Poulenc Rorer Sa | Peptides antagonistes de la neurotensine. |
| DE10226921A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Antibakterielle Amid-Makrozyklen |
| DE10234422A1 (de) * | 2002-07-29 | 2004-02-12 | Bayer Ag | Antibakterielle Ester-Makrozyklen |
| CA2540646A1 (en) * | 2003-10-01 | 2005-04-14 | Bayer Healthcare Ag | Antibacterial amide macrocycles |
| DE10358824A1 (de) * | 2003-12-16 | 2005-07-21 | Bayer Healthcare Ag | Antibakterielle Makrozyklen mit substituiertem Biphenyl |
| DE102005014240A1 (de) * | 2004-09-24 | 2006-03-30 | Bayer Healthcare Ag | Antibakterielle Amid-Makrozyklen IV |
-
2005
- 2005-03-30 DE DE102005014245A patent/DE102005014245A1/de not_active Withdrawn
-
2006
- 2006-03-22 ZA ZA200709336A patent/ZA200709336B/xx unknown
- 2006-03-22 RU RU2007139760/04A patent/RU2409588C2/ru not_active IP Right Cessation
- 2006-03-22 AU AU2006228751A patent/AU2006228751A1/en not_active Abandoned
- 2006-03-22 KR KR1020077025008A patent/KR20070116169A/ko not_active Ceased
- 2006-03-22 UA UAA200711765A patent/UA91541C2/ru unknown
- 2006-03-22 CN CNA2006800188391A patent/CN101228182A/zh active Pending
- 2006-03-22 EP EP06723614A patent/EP1869068A1/de not_active Withdrawn
- 2006-03-22 JP JP2008503408A patent/JP2008534540A/ja not_active Withdrawn
- 2006-03-22 CA CA002602755A patent/CA2602755A1/en not_active Abandoned
- 2006-03-22 WO PCT/EP2006/002617 patent/WO2006103015A1/de not_active Ceased
- 2006-03-22 NZ NZ562003A patent/NZ562003A/en unknown
- 2006-03-22 BR BRPI0612219-1A patent/BRPI0612219A2/pt not_active IP Right Cessation
- 2006-03-22 MX MX2007012146A patent/MX2007012146A/es not_active Application Discontinuation
-
2007
- 2007-09-11 IL IL185899A patent/IL185899A0/en unknown
- 2007-09-28 US US11/906,088 patent/US20080275018A1/en not_active Abandoned
- 2007-10-15 NO NO20075270A patent/NO20075270L/no not_active Application Discontinuation
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