CZ20014362A3 - 4´-Demykarosyl-8a-aza-8a-homotylosiny a způsob jejich výroby - Google Patents

4´-Demykarosyl-8a-aza-8a-homotylosiny a způsob jejich výroby Download PDF

Info

Publication number: CZ20014362A3
Authority: CZ; Czechia
Prior art keywords: och; coch; aza; demycarosyl; hydrogen
Prior art date: 1999-06-11

Application number

CZ20014362A

Other languages

Czech (cs)

English (en)

Inventor

Nevenka Lopotar

Amalija Narandja

Stjepan Mutak

Original Assignee

Pliva, Farmaceutska Industrija, Dioničko Dru©Tvo

Priority date (The priority date 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 date listed.)

1999-06-11

Filing date

2000-06-06

Publication date

2002-04-17

2000-06-06 Application filed by Pliva, Farmaceutska Industrija, Dioničko Dru©Tvo filed Critical Pliva, Farmaceutska Industrija, Dioničko Dru©Tvo

2002-04-17 Publication of CZ20014362A3 publication Critical patent/CZ20014362A3/cs

Links

238000004519 manufacturing process Methods 0.000 title description 2
125000002252 acyl group Chemical group 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 52
239000001257 hydrogen Substances 0.000 claims description 52
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
150000002431 hydrogen Chemical class 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims 1
238000000034 method Methods 0.000 abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 11
230000000844 anti-bacterial effect Effects 0.000 abstract description 3
238000002360 preparation method Methods 0.000 abstract description 3
239000003242 anti bacterial agent Substances 0.000 abstract description 2
229940088710 antibiotic agent Drugs 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
239000000047 product Substances 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
150000001875 compounds Chemical class 0.000 description 29
238000001819 mass spectrum Methods 0.000 description 22
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
238000003818 flash chromatography Methods 0.000 description 16
239000000741 silica gel Substances 0.000 description 16
229910002027 silica gel Inorganic materials 0.000 description 16
239000002904 solvent Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000012043 crude product Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
239000000284 extract Substances 0.000 description 7
238000002955 isolation Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 6
238000006140 methanolysis reaction Methods 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
150000001241 acetals Chemical class 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 4
229940125904 compound 1 Drugs 0.000 description 3
229940126214 compound 3 Drugs 0.000 description 3
238000000605 extraction Methods 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
230000006179 O-acylation Effects 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
239000005457 ice water Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
238000003833 Wallach reaction Methods 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
-1 atom hydrogen Chemical class 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
FEKRFYZGYUTGRY-UHFFFAOYSA-N n'-ethylmethanediimine Chemical compound CCN=C=N FEKRFYZGYUTGRY-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Saccharide Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CZ20014362A 1999-06-11 2000-06-06 4´-Demykarosyl-8a-aza-8a-homotylosiny a způsob jejich výroby CZ20014362A3 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HR990192A HRP990192A2 (en)	1999-06-11	1999-06-11	4'-DEMICAROZYL-8a-AZA-8a-HOMOTHILOSINE DERIVATIVES

Publications (1)

Publication Number	Publication Date
CZ20014362A3 true CZ20014362A3 (cs)	2002-04-17

Family

ID=10946940

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ20014362A CZ20014362A3 (cs)	1999-06-11	2000-06-06	4´-Demykarosyl-8a-aza-8a-homotylosiny a způsob jejich výroby

Country Status (13)

Country	Link
EP (1)	EP1189914A1 (fr)
JP (1)	JP2003502338A (fr)
AU (1)	AU767543B2 (fr)
CA (1)	CA2375812A1 (fr)
CZ (1)	CZ20014362A3 (fr)
EA (1)	EA200200026A1 (fr)
HR (1)	HRP990192A2 (fr)
HU (1)	HUP0201610A3 (fr)
NO (1)	NO322424B1 (fr)
SK (1)	SK17572001A3 (fr)
UA (1)	UA66930C2 (fr)
WO (1)	WO2000077016A1 (fr)
YU (1)	YU87401A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7091196B2 (en)	2002-09-26	2006-08-15	Rib-X Pharmaceuticals, Inc.	Bifunctional heterocyclic compounds and methods of making and using same
WO2004078770A1 (fr) *	2003-03-05	2004-09-16	Rib-X Pharmaceuticals, Inc.	Composes heterocycliques bifonctionnels et leurs procedes d'obtention et d'utilisation
WO2005019238A1 (fr)	2003-08-22	2005-03-03	Meiji Seika Kaisha, Ltd.	Nouveaux derives d'azalide et d'azalactam et procede permettant de produire ces derives
WO2005085266A2 (fr)	2004-02-27	2005-09-15	Rib-X Pharmaceuticals, Inc.	Composes macrocycliques et leurs procedes de fabrication et d'utilisation

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
YU45033B (en) *	1987-04-14	1991-06-30	Pliva Zagreb	Process for preparing 10,11,12,13-tetrahydro derivative
YU149889A (en) *	1989-07-26	1991-02-28	Pliva Zagreb	Process for preparing biologically active derivatives of tylozine
CZ211798A3 (cs) *	1997-07-16	1999-02-17	Pliva, Farmaceutska, Kemijska, Prehrambena I Kozmetička Industrije, Dioničko Društvo	Lineární 8a-sekoazalidy a způsob jejich výroby

1999
- 1999-06-11 HR HR990192A patent/HRP990192A2/hr not_active Application Discontinuation
2000
- 2000-06-06 YU YU87401A patent/YU87401A/sh unknown
- 2000-06-06 SK SK1757-2001A patent/SK17572001A3/sk unknown
- 2000-06-06 CA CA002375812A patent/CA2375812A1/fr not_active Abandoned
- 2000-06-06 JP JP2001503873A patent/JP2003502338A/ja active Pending
- 2000-06-06 WO PCT/HR2000/000018 patent/WO2000077016A1/fr not_active Ceased
- 2000-06-06 AU AU55583/00A patent/AU767543B2/en not_active Ceased
- 2000-06-06 HU HU0201610A patent/HUP0201610A3/hu unknown
- 2000-06-06 CZ CZ20014362A patent/CZ20014362A3/cs unknown
- 2000-06-06 EA EA200200026A patent/EA200200026A1/ru unknown
- 2000-06-06 UA UA2001129085A patent/UA66930C2/uk unknown
- 2000-06-06 EP EP00940676A patent/EP1189914A1/fr not_active Withdrawn
2001
- 2001-12-10 NO NO20016030A patent/NO322424B1/no unknown

Also Published As

Publication number	Publication date
EA200200026A1 (ru)	2002-06-27
NO322424B1 (no)	2006-10-02
JP2003502338A (ja)	2003-01-21
AU5558300A (en)	2001-01-02
CA2375812A1 (fr)	2000-12-21
HRP990192A2 (en)	2001-04-30
AU767543B2 (en)	2003-11-13
SK17572001A3 (sk)	2002-04-04
HUP0201610A3 (en)	2003-03-28
EP1189914A1 (fr)	2002-03-27
NO20016030D0 (no)	2001-12-10
WO2000077016A1 (fr)	2000-12-21
UA66930C2 (uk)	2004-06-15
HUP0201610A2 (en)	2002-10-28
YU87401A (sh)	2004-07-15
NO20016030L (no)	2002-01-30

Publication	Publication Date	Title
EP0287082B1 (fr)	1994-03-23	Dérivés de la tylosine et de la 10,11,12,13-tétrahydrotylosine, leur méthode de préparation et leur utilisation dans des compositions pharmaceutiques et dans la préparation de celles-ci
US5434140A (en)	1995-07-18	9-deoxo-9a-aza-11-deoxy-9a-homoerythromycin a 9a,11-cyclic carbamates
CZ20014362A3 (cs)	2002-04-17	4´-Demykarosyl-8a-aza-8a-homotylosiny a způsob jejich výroby
EP2354147A2 (fr)	2011-08-10	Antibiotiques à macrolide substituée 10
DE602004003054T2 (de)	2007-06-06	Neue 3-decladinosyl-9a-n-carbamoyl- und 9a-n-thiocarbamoylderivate von 9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin a
RU2234510C2 (ru)	2004-08-20	Производные класса олеандомицина и способ их получения
US5721346A (en)	1998-02-24	Compounds of the secomacrolide and secoazalide class and a process for the preparation thereof
RU2158268C2 (ru)	2000-10-27	Секомакролиды класса эритромицинов и способ их получения
Heggelund et al.	2007	Preparation of cyclic 2′, 3′-carbamate derivatives of erythromycin macrolide antibiotics
JPH10130296A (ja)	1998-05-19	チロシンの新規ポリヒドロ誘導体及びその製造方法
EP0490311B1 (fr)	1996-03-20	Dérivés de 10,11,12,13-tetra-hydrodesmycosin, procédé pour leur préparation, et leur utilisation dans la production des pharmaceutiques
HK1016989A (en)	1999-11-12	New secomacrolides from class of erythromycins and process for their preparation
PL182429B1 (pl)	2002-01-31	Pochodne 12,13-epoksy-tylozyny i sposób ich wytwarzania