CN85103908A - 制备4′-表多克索红菌素的新方法 - Google Patents

制备4′-表多克索红菌素的新方法 Download PDF

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Publication number: CN85103908A
Authority: CN; China
Prior art keywords: solution; biao; daunorubicin; dissolved; duokesuo
Prior art date: 1985-06-08
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.): Pending

Application number

CN198585103908A

Other languages

English (en)

Chinese (zh)

Inventor

费德里克·阿卡莫尼

塞吉欧·彭克

安东尼诺·苏阿拉诺

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Italia SRL

Original Assignee

Farmitalia Carlo Erba SRL

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.)

1985-07-16

Filing date

1985-06-08

Publication date

1986-11-05

1985-06-08 Application filed by Farmitalia Carlo Erba SRL filed Critical Farmitalia Carlo Erba SRL

1986-11-05 Publication of CN85103908A publication Critical patent/CN85103908A/zh

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 20
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims abstract description 13
229960000975 daunorubicin Drugs 0.000 claims abstract description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052794 bromium Inorganic materials 0.000 claims abstract description 6
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims abstract description 5
239000004280 Sodium formate Substances 0.000 claims abstract description 4
230000007062 hydrolysis Effects 0.000 claims abstract description 4
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
238000002360 preparation method Methods 0.000 claims abstract description 4
235000019254 sodium formate Nutrition 0.000 claims abstract description 4
VOASREXNXKOKBP-HWJSKKJZSA-N n-[(2s,3s,4s,6r)-6-[[(1s,3s)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1h-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]-2,2,2-trifluoroacetamide Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 VOASREXNXKOKBP-HWJSKKJZSA-N 0.000 claims abstract 2
238000011916 stereoselective reduction Methods 0.000 claims abstract 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 25
239000000243 solution Substances 0.000 claims description 23
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 22
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
239000011541 reaction mixture Substances 0.000 claims description 9
239000007864 aqueous solution Substances 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
239000011259 mixed solution Substances 0.000 claims description 6
239000003513 alkali Substances 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
239000002585 base Substances 0.000 claims description 3
229930182478 glucoside Natural products 0.000 claims description 3
150000008131 glucosides Chemical class 0.000 claims description 3
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 2
238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
230000001590 oxidative effect Effects 0.000 claims 1
229910000033 sodium borohydride Inorganic materials 0.000 claims 1
239000012279 sodium borohydride Substances 0.000 claims 1
239000002994 raw material Substances 0.000 abstract description 6
STQGQHZAVUOBTE-RPDDNNBZSA-N (7s,9s)-9-acetyl-7-[(2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 STQGQHZAVUOBTE-RPDDNNBZSA-N 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
NAALWFYYHHJEFQ-ZASNTINBSA-N (2s,5r,6r)-6-[[(2r)-2-[[6-[4-[bis(2-hydroxyethyl)sulfamoyl]phenyl]-2-oxo-1h-pyridine-3-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC(O)=CC=1)C(=O)C(C(N1)=O)=CC=C1C1=CC=C(S(=O)(=O)N(CCO)CCO)C=C1 NAALWFYYHHJEFQ-ZASNTINBSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000000605 extraction Methods 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
238000005406 washing Methods 0.000 description 4
WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
229960003109 daunorubicin hydrochloride Drugs 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
-1 Doxorubicin ketone Chemical class 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229960001866 silicon dioxide Drugs 0.000 description 2
SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000118 anti-neoplastic effect Effects 0.000 description 1
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical group O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 1
OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000003795 desorption Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229960004679 doxorubicin Drugs 0.000 description 1
AOJJSUZBOXZQNB-TZSSRYMLSA-N doxorubicine Natural products O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000021962 pH elevation Effects 0.000 description 1
230000005298 paramagnetic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
238000005204 segregation Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
238000010129 solution processing Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

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

CN198585103908A 1985-07-16 1985-06-08 制备4′-表多克索红菌素的新方法 Pending CN85103908A (zh)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB858517923A GB8517923D0 (en)	1985-07-16	1985-07-16	Distamycin derivatives

Publications (1)

Publication Number	Publication Date
CN85103908A true CN85103908A (zh)	1986-11-05

Family

ID=10582358

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CN198585103908A Pending CN85103908A (zh)	1985-07-16	1985-06-08	制备4′-表多克索红菌素的新方法
CN86104774A Expired - Fee Related CN1026984C (zh)	1985-07-16	1986-07-16	偏端霉素衍生物的制备方法

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CN86104774A Expired - Fee Related CN1026984C (zh)	1985-07-16	1986-07-16	偏端霉素衍生物的制备方法

Country Status (29)

Country	Link
US (1)	US4738980A (2)
JP (1)	JPH0780842B2 (2)
KR (1)	KR940003495B1 (2)
CN (2)	CN85103908A (2)
AT (1)	AT386822B (2)
AU (1)	AU584723B2 (2)
BE (1)	BE905109A (2)
CA (1)	CA1247627A (2)
CH (1)	CH671958A5 (2)
CZ (1)	CZ277823B6 (2)
DE (1)	DE3623853C2 (2)
DK (1)	DK335886A (2)
ES (1)	ES2000346A6 (2)
FI (1)	FI82929C (2)
FR (1)	FR2585019B1 (2)
GB (2)	GB8517923D0 (2)
GR (1)	GR861840B (2)
HU (1)	HU198087B (2)
IE (1)	IE59275B1 (2)
IL (1)	IL79401A (2)
IT (1)	IT1213103B (2)
NL (1)	NL8601838A (2)
NO (1)	NO169014C (2)
NZ (1)	NZ216828A (2)
PH (1)	PH23459A (2)
PT (1)	PT82985B (2)
SE (1)	SE468594B (2)
SU (2)	SU1535378A3 (2)
ZA (1)	ZA865262B (2)

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Publication number	Priority date	Publication date	Assignee	Title
CN107683284A (zh) *	2015-03-30	2018-02-09	明治制果药业株式会社	表柔比星的制造方法及其新的制造中间体

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SE468642B (sv) *	1985-07-16	1993-02-22	Erba Farmitalia	Poly-4-aminopyrrol-2-karboxamidoderivat och foerfarande foer deras framstaellning och en farmaceutisk komposition
US5310752A (en) *	1986-05-20	1994-05-10	Farmitalia Carlo Erba Spa	Site specific alkylating agents
US5049579A (en) *	1986-05-20	1991-09-17	Farmitalia Carlo Erba, S.R.L.	Site specific alkylating agents
GB8612218D0 (en) *	1986-05-20	1986-06-25	Erba Farmitalia	Site specific alkylating agents
GB8906709D0 (en) *	1989-03-23	1989-05-10	Creighton Andrew M	Acryloyl substituted pyrrole derivatives
WO1992013838A1 (en) *	1991-02-06	1992-08-20	Synphar Laboratories, Inc.	Oligopeptide antiretroviral agents
IT1262921B (it) *	1992-01-10	1996-07-22	Federico Arcamone	Agenti antitumorali analoghi di oligopeptidi pirrol-amidinici retroversi processi di preparazione e prodotti farmaceutici che li contengono
DE4205948C2 (de) *	1992-02-24	1996-10-31	Mannesmann Ag	Farbbandkassette für ein endloses Farbband
US5273991A (en) *	1992-07-29	1993-12-28	Research Corporation Technologies, Inc.	Imidazole-containing compositions and methods of use thereof analogs of distamycin
EP0792262A2 (en) *	1994-11-14	1997-09-03	Nzym, Inc.	Methods and compositions for treating phytopathogenic fungi infections
US5637621A (en) *	1994-11-14	1997-06-10	Nzym, Inc.	Methods and compositions for treating Botrytis infections
US5629348A (en) *	1994-11-14	1997-05-13	Nzym, Inc.	Methods and compositions for treating septoria infections
DE19805431A1 (de) *	1998-02-11	1999-08-12	Merck Patent Gmbh	Heteroaromatische Oligoamide als Affinitätsliganden
CA2403537A1 (en) *	2000-03-16	2001-10-11	Genesoft, Inc.	Charged compounds comprising a nucleic acid binding moiety and uses therefor
US7078536B2 (en) *	2001-03-14	2006-07-18	Genesoft Pharmaceuticals, Inc.	Charged compounds comprising a nucleic acid binding moiety and uses therefor
GB0015447D0 (en) *	2000-06-23	2000-08-16	Pharmacia & Upjohn Spa	Combined therapy against tumors comprising substituted acryloyl derivates and alkylating agents
ITTO20010633A1 (it) *	2001-07-02	2003-01-02	Univ Ferrara	Nuovo impiego di poliammidi eterocicliche e benzoeterocicliche strutturalmente correlate all'antibiotico naturale distamicina a.
ATE425753T1 (de)	2002-08-02	2009-04-15	Genesoft Pharmaceuticals Inc	Biaryl-verbindungen mit antiinfektiver wirkung
EP1562931A2 (en) *	2002-10-25	2005-08-17	Genesoft Pharmaceuticals, Inc.	Anti-infective biaryl compounds
JP2006509027A (ja) *	2002-12-10	2006-03-16	オーシェントファーマシューティカルズコーポレーション	（ピロールカルボキサミド）−（ベンズアミド）−（イミダゾールカルボキサミド）モチーフを有する抗菌化合物
WO2005051318A2 (en) *	2003-11-24	2005-06-09	Viropharma Incorporated	Compounds, compositions and methods for treatment and prophylaxis of hepatitis c viral infections and associated diseases

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CA557568A (en) *		1958-05-20	J. Weiss Martin	Substituted aminopyrrolecarboxylic acids and esters
CA547128A (en) *		1957-10-08	W. Waller Coy	Substituted pyrrolecarboxamidopyrroles
FR86210E (2) *	1963-04-04	1966-03-23
DE1795539A1 (de) *	1963-07-26	1972-01-13	Farmaceutici Italia	Verfahren zur Herstellung von neuen Pyrrolderivaten und ihren Salzen
DE1470284B1 (de) *	1963-07-26	1971-12-16	Farmaceutici Italia	Beta-{1-Methyl-4-[1-methyl-4-(1-methyl-4-formylamino-pyrrol-2-carboxamido)-pyrrol-2-carboxamido]-pyrrol-2-carboxamido}-propionamidin sowie dessen Saeureadditionssalze
FR141F (fr) *	1963-07-26	1965-07-08	Farmaceutici Italia	Nouveaux dérivés du pyrrol
BE666612A (2) *	1963-07-26	1965-11-03
NL130086C (2) *	1964-07-14	1970-06-15
SE468642B (sv) *	1985-07-16	1993-02-22	Erba Farmitalia	Poly-4-aminopyrrol-2-karboxamidoderivat och foerfarande foer deras framstaellning och en farmaceutisk komposition
GB8612218D0 (en) *	1986-05-20	1986-06-25	Erba Farmitalia	Site specific alkylating agents

1985
- 1985-06-08 CN CN198585103908A patent/CN85103908A/zh active Pending
- 1985-07-16 GB GB858517923A patent/GB8517923D0/en active Pending
- 1985-10-03 US US06/783,508 patent/US4738980A/en not_active Expired - Fee Related
1986
- 1986-07-11 SE SE8603099A patent/SE468594B/sv not_active IP Right Cessation
- 1986-07-11 AT AT0188786A patent/AT386822B/de not_active IP Right Cessation
- 1986-07-14 HU HU862903A patent/HU198087B/hu not_active IP Right Cessation
- 1986-07-14 NZ NZ216828A patent/NZ216828A/xx unknown
- 1986-07-14 ES ES8600291A patent/ES2000346A6/es not_active Expired
- 1986-07-14 IL IL79401A patent/IL79401A/xx not_active IP Right Cessation
- 1986-07-14 IE IE187486A patent/IE59275B1/en not_active IP Right Cessation
- 1986-07-14 NL NL8601838A patent/NL8601838A/xx not_active Application Discontinuation
- 1986-07-14 AU AU60203/86A patent/AU584723B2/en not_active Ceased
- 1986-07-15 IT IT8621124A patent/IT1213103B/it active
- 1986-07-15 PH PH34013A patent/PH23459A/en unknown
- 1986-07-15 NO NO862861A patent/NO169014C/no unknown
- 1986-07-15 DE DE3623853A patent/DE3623853C2/de not_active Expired - Fee Related
- 1986-07-15 DK DK335886A patent/DK335886A/da not_active Application Discontinuation
- 1986-07-15 KR KR1019860005716A patent/KR940003495B1/ko not_active Expired - Fee Related
- 1986-07-15 BE BE0/216923A patent/BE905109A/fr not_active IP Right Cessation
- 1986-07-15 SU SU864027842A patent/SU1535378A3/ru active
- 1986-07-15 JP JP61164878A patent/JPH0780842B2/ja not_active Expired - Lifetime
- 1986-07-15 CA CA000513756A patent/CA1247627A/en not_active Expired
- 1986-07-15 CH CH2821/86A patent/CH671958A5/de not_active IP Right Cessation
- 1986-07-15 ZA ZA865262A patent/ZA865262B/xx unknown
- 1986-07-15 FR FR868610295A patent/FR2585019B1/fr not_active Expired
- 1986-07-15 GR GR861840A patent/GR861840B/el unknown
- 1986-07-15 PT PT82985A patent/PT82985B/pt not_active IP Right Cessation
- 1986-07-16 FI FI862960A patent/FI82929C/fi not_active IP Right Cessation
- 1986-07-16 CN CN86104774A patent/CN1026984C/zh not_active Expired - Fee Related
- 1986-07-16 GB GB8617293A patent/GB2178037B/en not_active Expired
- 1986-07-16 CZ CS865411A patent/CZ277823B6/cs unknown
1987
- 1987-11-11 SU SU874203631A patent/SU1538893A3/ru active

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN107683284A (zh) *	2015-03-30	2018-02-09	明治制果药业株式会社	表柔比星的制造方法及其新的制造中间体

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Publication number	Publication date
NO862861D0 (no)	1986-07-15
SU1538893A3 (ru)	1990-01-23
CN86104774A (zh)	1987-02-11
DE3623853C2 (de)	1995-12-21
BE905109A (fr)	1987-01-15
DK335886D0 (da)	1986-07-15
GB2178037A (en)	1987-02-04
NO169014C (no)	1992-04-29
CS541186A3 (en)	1992-09-16
FI862960L (fi)	1987-01-17
ATA188786A (de)	1988-03-15
SU1535378A3 (ru)	1990-01-07
IT1213103B (it)	1989-12-07
AU584723B2 (en)	1989-06-01
FI862960A0 (fi)	1986-07-16
CA1247627A (en)	1988-12-28
JPH0780842B2 (ja)	1995-08-30
IL79401A (en)	1991-05-12
PT82985B (pt)	1989-01-30
GB8517923D0 (en)	1985-08-21
CH671958A5 (2)	1989-10-13
IE861874L (en)	1987-01-16
DK335886A (da)	1987-01-17
PT82985A (pt)	1986-08-01
SE8603099L (sv)	1987-01-17
NL8601838A (nl)	1987-02-16
IT8621124A0 (it)	1986-07-15
AU6020386A (en)	1987-01-22
KR940003495B1 (ko)	1994-04-23
DE3623853A1 (de)	1987-01-29
NZ216828A (en)	1989-11-28
SE468594B (sv)	1993-02-15
CZ277823B6 (en)	1993-06-16
IE59275B1 (en)	1994-02-09
GB2178037B (en)	1989-07-26
GB8617293D0 (en)	1986-08-20
HUT41814A (en)	1987-05-28
ES2000346A6 (es)	1988-02-16
KR870001228A (ko)	1987-03-12
JPS6230755A (ja)	1987-02-09
FR2585019A1 (fr)	1987-01-23
HU198087B (en)	1989-07-28
ZA865262B (en)	1987-03-25
NO169014B (no)	1992-01-20
FR2585019B1 (fr)	1989-07-13
CN1026984C (zh)	1994-12-14
SE8603099D0 (sv)	1986-07-11
FI82929C (fi)	1991-05-10
US4738980A (en)	1988-04-19
AT386822B (de)	1988-10-25
PH23459A (en)	1989-08-07
GR861840B (en)	1986-11-18
NO862861L (no)	1987-01-19
FI82929B (fi)	1991-01-31
IL79401A0 (en)	1986-10-31

Legal Events

Date	Code	Title
1985-10-10	C10	Entry into substantive examination
1985-10-10	SE01	Entry into force of request for substantive examination
1986-11-05	C06	Publication
1986-11-05	PB01	Publication
1988-02-10	WD01	Invention patent application deemed withdrawn after publication

Publication	Publication Date	Title
CN85103908A (zh)	1986-11-05	制备4′-表多克索红菌素的新方法
Tann et al.	1985	Fluorocarbohydrates in synthesis. An efficient synthesis of 1-(2-deoxy-2-fluoro-. beta.-D-arabinofuranosyl)-5-iodouracil (. beta.-FIAU) and 1-(2-deoxy-2-fluoro-. beta.-D-arabinofuranosyl) thymine (. beta.-FMAU)
CA1239639A (en)	1988-07-26	Epimeric azahomoerythromycin a derivative and intermediates therefor
EP1189915B1 (en)	2006-07-26	Process for the production of azithromycin
US4772334A (en)	1988-09-20	Process for producing highly pure rhamnose from gum arabic
Choi et al.	1968	Neuramine-lactose, neuramine-lactose sulfate, and lactose sulfate from rat mammary glands. Isolation, purification, and permethylation studies
CA1075234A (en)	1980-04-08	Antibiotic substances derived from antibiotic 67-694 and processes for their preparation
JPS6012039B2 (ja)	1985-03-29	新規抗生物質その製法および抗菌性および抗カビ性組成物
NO162023B (no)	1989-07-17	Fremgangsmaate til fremstilling av antracyklinderivater.
Richtmyer	1970	The isolation of volemitol and other polyhydric alcohols from avocado seeds
Stevens et al.	1966	Hydroxylation of ethyl 2, 3-didehydro-2, 3-dideoxy-α-D-glucopyranoside
US4159990A (en)	1979-07-03	Reduction of 2,5-diketogluconic acid
JPS6219429B2 (2)	1987-04-28
JP2001008694A (ja)	2001-01-16	Ｄ−キロ−イノシトールの新規製造方法
KR900007318B1 (ko)	1990-10-08	4'-에피독소루비신의 제조방법
CH632769A5 (de)	1982-10-29	Verfahren zur herstellung von anthracyclinen.
Feather et al.	1972	A highly branched exocellular D-glucan from Monolinia fructicola
Mamedova et al.	2002	Triterpene glycosides of Astragalus and their genins. LXVII. Structure of cycloexoside B
JPH055837B2 (2)	1993-01-25
US4855414A (en)	1989-08-08	Process for production of anthracycline compound R20X2
CN120484032A (zh)	2025-08-15	一种2-脱氧糖及其制备方法
JPS62293A (ja)	1987-01-06	Ｌ−ラムノ−スの製造法
US3573275A (en)	1971-03-30	Isolation and purification of coumermycin antibiotics
JP4410914B2 (ja)	2010-02-10	Ｌ−キロ−１−イノソースの新規製造方法
Ballentine et al.	1944	An Unidentified Growth Factor for a Gas Gangrene CLOSTRIDIUM1

CN85103908A - 制备4′-表多克索红菌素的新方法 - Google Patents

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