SK94998A3 - Linear 8a-seco azalides and method for producing thereof - Google Patents

Linear 8a-seco azalides and method for producing thereof Download PDF

Info

Publication number: SK94998A3
Authority: SK; Slovakia
Prior art keywords: linear; represent; line; hydrogen; group
Prior art date: 1997-07-16

Application number

SK949-98A

Other languages

English (en)

Slovak (sk)

Inventor

Nevenka Lopotar

Amalija Narandja

Zoran Mandic

Original Assignee

Pliva Pharm & Chem Works

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.)

1997-07-16

Filing date

1998-07-10

Publication date

1999-02-11

1997-07-16 Priority claimed from HRP970386 external-priority patent/HRP970386A2/hr

1998-05-22 Priority claimed from HR980276A external-priority patent/HRP980276A2/hr

1998-07-10 Application filed by Pliva Pharm & Chem Works filed Critical Pliva Pharm & Chem Works

1999-02-11 Publication of SK94998A3 publication Critical patent/SK94998A3/sk

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 12
125000002252 acyl group Chemical group 0.000 claims abstract description 10
-1 hydroxyimino group Chemical group 0.000 claims abstract description 6
125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 5
238000007126 N-alkylation reaction Methods 0.000 claims abstract description 4
238000006146 oximation reaction Methods 0.000 claims abstract description 4
230000006179 O-acylation Effects 0.000 claims abstract description 3
125000000468 ketone group Chemical group 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 41
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 32
150000002431 hydrogen Chemical class 0.000 claims description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 22
125000004430 oxygen atom Chemical group O* 0.000 claims description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
235000019253 formic acid Nutrition 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
238000010992 reflux Methods 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
238000006722 reduction reaction Methods 0.000 claims description 5
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
150000008282 halocarbons Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
229910000510 noble metal Inorganic materials 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
229960000583 acetic acid Drugs 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
238000010531 catalytic reduction reaction Methods 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
239000012362 glacial acetic acid Substances 0.000 claims description 3
239000010439 graphite Substances 0.000 claims description 3
229910002804 graphite Inorganic materials 0.000 claims description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
229910052753 mercury Inorganic materials 0.000 claims description 3
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000008363 phosphate buffer Substances 0.000 claims description 3
229910003446 platinum oxide Inorganic materials 0.000 claims description 3
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims description 2
239000012528 membrane Substances 0.000 claims description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
238000009835 boiling Methods 0.000 claims 1
238000006140 methanolysis reaction Methods 0.000 claims 1
238000007070 tosylation reaction Methods 0.000 claims 1
230000002829 reductive effect Effects 0.000 abstract description 18
229930194936 Tylosin Natural products 0.000 abstract description 4
235000019375 tylosin Nutrition 0.000 abstract description 4
150000003951 lactams Chemical class 0.000 abstract description 3
235000018734 Sambucus australis Nutrition 0.000 abstract 2
244000180577 Sambucus australis Species 0.000 abstract 2
125000003277 amino group Chemical group 0.000 abstract 1
238000005984 hydrogenation reaction Methods 0.000 abstract 1
150000002576 ketones Chemical class 0.000 abstract 1
239000000047 product Substances 0.000 description 25
238000001819 mass spectrum Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000002026 chloroform extract Substances 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
238000000605 extraction Methods 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229940125904 compound 1 Drugs 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000002904 solvent Substances 0.000 description 5
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
239000004182 Tylosin Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 3
229960004059 tylosin Drugs 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
229940125773 compound 10 Drugs 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000003797 solvolysis reaction Methods 0.000 description 2
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-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
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
VXZBYIWNGKSFOJ-UHFFFAOYSA-N 2-[4-[5-(2,3-dihydro-1H-inden-2-ylamino)pyrazin-2-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC=1N=CC(=NC=1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 VXZBYIWNGKSFOJ-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
241000531206 Faradaya Species 0.000 description 1
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Biotechnology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Crystallography & Structural Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)

SK949-98A 1997-07-16 1998-07-10 Linear 8a-seco azalides and method for producing thereof SK94998A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HRP970386 HRP970386A2 (en)	1997-07-16	1997-07-16	Novel seco compounds from a class of tylosins
HR980276A HRP980276A2 (en)	1998-05-22	1998-05-22	New secothylozine compounds

Publications (1)

Publication Number	Publication Date
SK94998A3 true SK94998A3 (en)	1999-02-11

Family

ID=26317103

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK949-98A SK94998A3 (en)	1997-07-16	1998-07-10	Linear 8a-seco azalides and method for producing thereof

Country Status (11)

Country	Link
US (1)	US5962661A (fr)
EP (1)	EP0891981A1 (fr)
JP (1)	JPH1192491A (fr)
CN (1)	CN1218811A (fr)
BG (1)	BG102631A (fr)
CA (1)	CA2240976A1 (fr)
CZ (1)	CZ211798A3 (fr)
HU (1)	HUP9801594A3 (fr)
NO (1)	NO983267D0 (fr)
PL (1)	PL327389A1 (fr)
SK (1)	SK94998A3 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HRP990192A2 (en) *	1999-06-11	2001-04-30	Pliva D D	4'-DEMICAROZYL-8a-AZA-8a-HOMOTHILOSINE DERIVATIVES

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SI8710674B (sl) *	1987-04-14	1998-06-30	Pliva	Postopek za pripravo 10,11,12,13-tetrahidro derivatov tilozina
YU149889A (en) *	1989-07-26	1991-02-28	Pliva Zagreb	Process for preparing biologically active derivatives of tylozine
US5215980A (en) *	1992-01-17	1993-06-01	Merck & Co., Inc.	10-AZA-9-deoxo-11-deoxy-erythromycin A and derivatives thereof
HRP950145A2 (en) *	1995-03-27	1997-08-31	Sour Pliva	New compounds of the secomacrolide and secoazalide class and a process for the preparation thereof
HRP970141A2 (en) *	1997-03-12	1999-02-28	Banić-Tomaueić Zrinka	New secomacrolydes of erythromicin a, and a process for the preparation thereof

1998
- 1998-07-03 CZ CZ982117A patent/CZ211798A3/cs unknown
- 1998-07-10 SK SK949-98A patent/SK94998A3/sk unknown
- 1998-07-10 PL PL98327389A patent/PL327389A1/xx unknown
- 1998-07-10 EP EP98112904A patent/EP0891981A1/fr not_active Withdrawn
- 1998-07-13 CA CA002240976A patent/CA2240976A1/fr not_active Abandoned
- 1998-07-14 US US09/114,514 patent/US5962661A/en not_active Expired - Fee Related
- 1998-07-15 HU HU9801594A patent/HUP9801594A3/hu unknown
- 1998-07-15 CN CN98117423A patent/CN1218811A/zh active Pending
- 1998-07-15 JP JP10214775A patent/JPH1192491A/ja active Pending
- 1998-07-15 BG BG102631A patent/BG102631A/xx unknown
- 1998-07-15 NO NO983267A patent/NO983267D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
HUP9801594A3 (en)	2000-03-28
CN1218811A (zh)	1999-06-09
US5962661A (en)	1999-10-05
PL327389A1 (en)	1999-01-18
HUP9801594A2 (hu)	1999-02-01
EP0891981A1 (fr)	1999-01-20
BG102631A (en)	1999-09-30
JPH1192491A (ja)	1999-04-06
CA2240976A1 (fr)	1999-01-16
NO983267L (fr)	1999-01-18
HU9801594D0 (en)	1998-09-28
NO983267D0 (no)	1998-07-15
CZ211798A3 (cs)	1999-02-17

Publication	Publication Date	Title
US5112975A (en)	1992-05-12	Preparation of noroxymorphone from morphine
de Armas et al.	1988	Steroidal N-nitroamines. Part 4. Intramolecular functionalization of N-nitroamine radicals: synthesis of 1, 4-nitroimine compounds
EP0158476A1 (fr)	1985-10-16	Préparation de la noroxymorphone à partir de la morphine
EP0287082A2 (fr)	1988-10-19	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
DE69025505T2 (de)	1996-09-19	Tylosin-Derivate
CN114315755B (zh)	2023-10-10	一种Tubulysin及其类似物的关键中间体的合成方法
CN113698402B (zh)	2022-03-25	具有抗炎活性的天然生物碱Arbornamine的合成方法及应用
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