DD243285A5 - Verfahren zur herstellung kristallinen 7-(dimethylaminomethylen)-amino-9a-methoxymitosans - Google Patents

Verfahren zur herstellung kristallinen 7-(dimethylaminomethylen)-amino-9a-methoxymitosans Download PDF

Info

Publication number: DD243285A5
Authority: DD; German Democratic Republic
Prior art keywords: amino; dimethylaminomethylene; methoxymitosane; amorphous; mitomycin
Prior art date: 1985-02-21

Application number

DD86287197A

Other languages

German (de)

English (en)

Inventor

Murray A Kaplan

Dolatrai M Vyas

Original Assignee

��`��@��Kk��

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.)

1985-02-21

Filing date

1986-02-20

Publication date

1987-02-25

1986-02-20 Application filed by ��`��@��Kk�� filed Critical ��`��@��Kk��

1987-02-25 Publication of DD243285A5 publication Critical patent/DD243285A5/de

Links

-1 DIMETHYLAMINOMETHYLENE Chemical class 0.000 title claims abstract description 31
238000004519 manufacturing process Methods 0.000 title claims abstract description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 21
238000002425 crystallisation Methods 0.000 claims abstract 2
230000008025 crystallization Effects 0.000 claims abstract 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
238000002329 infrared spectrum Methods 0.000 claims description 4
239000003814 drug Substances 0.000 abstract description 2
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
229960004857 mitomycin Drugs 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
238000000034 method Methods 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000855 fermentation Methods 0.000 description 4
230000004151 fermentation Effects 0.000 description 4
229930192392 Mitomycin Natural products 0.000 description 3
HYFMSAFINFJTFH-UHFFFAOYSA-N Mitomycin-A Natural products O=C1C(OC)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)N2CC2NC21 HYFMSAFINFJTFH-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000003480 eluent Substances 0.000 description 3
HYFMSAFINFJTFH-NGSRAFSJSA-N mitomycin A Chemical compound O=C1C(OC)=C(C)C(=O)C2=C1[C@@H](COC(N)=O)[C@]1(OC)N2C[C@@H]2N[C@@H]21 HYFMSAFINFJTFH-NGSRAFSJSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
238000003828 vacuum filtration Methods 0.000 description 2
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
UZUUQCBCWDBYCG-UHFFFAOYSA-N Mitomycin B Natural products O=C1C(OC)=C(C)C(=O)C2=C1C(COC(N)=O)C1(O)N2CC2C1N2C UZUUQCBCWDBYCG-UHFFFAOYSA-N 0.000 description 1
HRHKSTOGXBBQCB-UHFFFAOYSA-N Mitomycin E Natural products O=C1C(N)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)C3N(C)C3CN12 HRHKSTOGXBBQCB-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
SEZWJRWTCIPRSV-UHFFFAOYSA-N [N]C(N)=O Chemical compound [N]C(N)=O SEZWJRWTCIPRSV-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
235000010633 broth Nutrition 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
235000019365 chlortetracycline Nutrition 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
206010061289 metastatic neoplasm Diseases 0.000 description 1
HRHKSTOGXBBQCB-VFWICMBZSA-N methylmitomycin Chemical compound O=C1C(N)=C(C)C(=O)C2=C1[C@@H](COC(N)=O)[C@@]1(OC)[C@H]3N(C)[C@H]3CN12 HRHKSTOGXBBQCB-VFWICMBZSA-N 0.000 description 1
UZUUQCBCWDBYCG-DQRAMIIBSA-N mitomycin B Chemical compound O=C1C(OC)=C(C)C(=O)C2=C1[C@H](COC(N)=O)[C@]1(O)N2C[C@H]2[C@@H]1N2C UZUUQCBCWDBYCG-DQRAMIIBSA-N 0.000 description 1
238000002638 palliative care Methods 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229950004406 porfiromycin Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Saccharide Compounds (AREA)
Luminescent Compositions (AREA)

DD86287197A 1985-02-21 1986-02-20 Verfahren zur herstellung kristallinen 7-(dimethylaminomethylen)-amino-9a-methoxymitosans DD243285A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/703,778 US4639528A (en)	1985-02-21	1985-02-21	Crystalline form of 7-(dimethylaminomethylene-amino-9a-methoxymitosane

Publications (1)

Publication Number	Publication Date
DD243285A5 true DD243285A5 (de)	1987-02-25

Family

ID=24826748

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86287197A DD243285A5 (de)	1985-02-21	1986-02-20	Verfahren zur herstellung kristallinen 7-(dimethylaminomethylen)-amino-9a-methoxymitosans

Country Status (33)

Country	Link
US (1)	US4639528A (fr)
JP (1)	JPS61194086A (fr)
KR (1)	KR930003075B1 (fr)
CN (1)	CN1013495B (fr)
AR (1)	AR241269A1 (fr)
AU (1)	AU595183B2 (fr)
BE (1)	BE904259A (fr)
CA (1)	CA1273635A (fr)
CH (1)	CH666687A5 (fr)
CY (1)	CY1587A (fr)
DD (1)	DD243285A5 (fr)
DE (1)	DE3605527A1 (fr)
DK (1)	DK163241C (fr)
EG (1)	EG17775A (fr)
ES (1)	ES8705249A1 (fr)
FI (1)	FI860720A7 (fr)
FR (1)	FR2577554B1 (fr)
GB (1)	GB2171406B (fr)
GR (1)	GR860510B (fr)
HK (1)	HK22291A (fr)
HU (1)	HU193628B (fr)
IT (1)	IT1188701B (fr)
LU (1)	LU86317A1 (fr)
MY (1)	MY101451A (fr)
NL (1)	NL8600432A (fr)
NO (1)	NO162021C (fr)
NZ (1)	NZ215017A (fr)
OA (1)	OA08207A (fr)
PT (1)	PT82059B (fr)
SE (1)	SE468596B (fr)
SU (1)	SU1375138A3 (fr)
YU (1)	YU44598B (fr)
ZA (1)	ZA86249B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA86308B (en) *	1985-02-25	1986-11-26	Bristol Myers Co	In-vial deposition of 7-(dimethylaminomethylene)amino-9a-methoxy-mitosane
JPS6335520A (ja) *	1986-07-31	1988-02-16	Kyowa Hakko Kogyo Co Ltd	抗腫瘍剤

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4156735A (en) *	1976-01-17	1979-05-29	Hoechst Aktiengesellschaft	Thiazolidine derivatives
IE45511B1 (en) *	1976-09-01	1982-09-08	Ciba Geigy Ag	New derivatives of perhydro-aza-heterocycles and processesfor the production thereof
JPS588397B2 (ja) *	1978-07-18	1983-02-15	協和醗酵工業株式会社	新規なマイトマイシン誘導体およびその製造法
DE3220378C2 (de) *	1982-05-29	1994-03-03	Heidelberger Druckmasch Ag	Steuervorrichtung für eine Druckmaschine
US4487769A (en) *	1982-06-04	1984-12-11	Bristol-Myers Company	Amidines
US4478769A (en) *	1982-09-30	1984-10-23	Amerace Corporation	Method for forming an embossing tool with an optically precise pattern

1985
- 1985-02-21 US US06/703,778 patent/US4639528A/en not_active Expired - Fee Related
1986
- 1986-01-02 CA CA000498870A patent/CA1273635A/fr not_active Expired - Lifetime
- 1986-01-13 ZA ZA86249A patent/ZA86249B/xx unknown
- 1986-02-03 NZ NZ215017A patent/NZ215017A/xx unknown
- 1986-02-05 CN CN86100944A patent/CN1013495B/zh not_active Expired
- 1986-02-11 FR FR868601815A patent/FR2577554B1/fr not_active Expired
- 1986-02-12 JP JP61028743A patent/JPS61194086A/ja active Pending
- 1986-02-18 IT IT19439/86A patent/IT1188701B/it active
- 1986-02-18 AU AU53685/86A patent/AU595183B2/en not_active Ceased
- 1986-02-18 FI FI860720A patent/FI860720A7/fi not_active Application Discontinuation
- 1986-02-19 ES ES552186A patent/ES8705249A1/es not_active Expired
- 1986-02-20 NL NL8600432A patent/NL8600432A/nl not_active Application Discontinuation
- 1986-02-20 SU SU864023029A patent/SU1375138A3/ru active
- 1986-02-20 DE DE19863605527 patent/DE3605527A1/de not_active Withdrawn
- 1986-02-20 OA OA58789A patent/OA08207A/fr unknown
- 1986-02-20 AR AR86303185A patent/AR241269A1/es active
- 1986-02-20 DK DK079886A patent/DK163241C/da not_active IP Right Cessation
- 1986-02-20 DD DD86287197A patent/DD243285A5/de not_active IP Right Cessation
- 1986-02-20 BE BE0/216293A patent/BE904259A/fr not_active IP Right Cessation
- 1986-02-20 SE SE8600778A patent/SE468596B/sv not_active IP Right Cessation
- 1986-02-20 NO NO860633A patent/NO162021C/no unknown
- 1986-02-20 PT PT82059A patent/PT82059B/pt not_active IP Right Cessation
- 1986-02-20 KR KR1019860001171A patent/KR930003075B1/ko not_active Expired - Fee Related
- 1986-02-20 HU HU86710A patent/HU193628B/hu not_active IP Right Cessation
- 1986-02-20 GB GB08604201A patent/GB2171406B/en not_active Expired
- 1986-02-20 LU LU86317A patent/LU86317A1/fr unknown
- 1986-02-20 CH CH679/86A patent/CH666687A5/de not_active IP Right Cessation
- 1986-02-20 EG EG84/86A patent/EG17775A/xx active
- 1986-02-20 YU YU258/86A patent/YU44598B/xx unknown
- 1986-02-21 GR GR860510A patent/GR860510B/el unknown
1987
- 1987-09-28 MY MYPI87002082A patent/MY101451A/en unknown
1991
- 1991-03-26 HK HK222/91A patent/HK22291A/xx unknown
1992
- 1992-04-03 CY CY1587A patent/CY1587A/en unknown

Also Published As

Publication number	Publication date
PT82059B (pt)	1988-07-01
PT82059A (en)	1986-03-01
GB2171406B (en)	1988-08-10
HU193628B (en)	1987-11-30
GB2171406A (en)	1986-08-28
ES552186A0 (es)	1987-05-01
FI860720A0 (fi)	1986-02-18
BE904259A (fr)	1986-08-20
OA08207A (fr)	1987-10-30
HK22291A (en)	1991-04-04
SE468596B (sv)	1993-02-15
CA1273635A (fr)	1990-09-04
AR241269A1 (es)	1992-04-30
JPS61194086A (ja)	1986-08-28
KR930003075B1 (ko)	1993-04-17
NO162021C (no)	1989-10-25
FI860720L (fi)	1986-08-22
CY1587A (en)	1992-04-03
CH666687A5 (de)	1988-08-15
DK163241B (da)	1992-02-10
FR2577554B1 (fr)	1989-12-29
NO860633L (no)	1986-08-22
AU595183B2 (en)	1990-03-29
SE8600778L (sv)	1986-08-22
YU44598B (en)	1990-10-31
CN86100944A (zh)	1986-11-05
EG17775A (en)	1991-06-30
NO162021B (no)	1989-07-17
GR860510B (en)	1986-06-24
FR2577554A1 (fr)	1986-08-22
GB8604201D0 (en)	1986-03-26
DE3605527A1 (de)	1986-08-21
US4639528A (en)	1987-01-27
IT8619439A0 (it)	1986-02-18
DK79886D0 (da)	1986-02-20
HUT40565A (en)	1987-01-28
IT1188701B (it)	1988-01-28
SU1375138A3 (ru)	1988-02-15
MY101451A (en)	1991-11-18
NL8600432A (nl)	1986-09-16
YU25886A (en)	1988-04-30
SE8600778D0 (sv)	1986-02-20
LU86317A1 (fr)	1986-09-02
DK79886A (da)	1986-08-22
ES8705249A1 (es)	1987-05-01
KR860006468A (ko)	1986-09-11
IT8619439A1 (it)	1987-08-18
DK163241C (da)	1992-06-29
AU5368586A (en)	1986-08-28
CN1013495B (zh)	1991-08-14
NZ215017A (en)	1989-06-28
FI860720A7 (fi)	1986-08-22
ZA86249B (en)	1986-08-27

Legal Events

Date	Code	Title	Description
1996-05-09	ENJ	Ceased due to non-payment of renewal fee

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DE69522490T2 (de)	2002-05-16	Platinkomplexe
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DE68929275T2 (de)	2001-05-23	CC-1065-Analoge mit zwei CPI-Subeinheiten
DE3446371C2 (fr)	1990-08-16
CH657856A5 (de)	1986-09-30	Mitosanverbindungen.
DE3413489C2 (fr)	1991-07-25
DE3613447C2 (fr)	1991-04-11
DE3133519A1 (de)	1982-06-09	"2-amino-3-carbethoxyamino-6-(p-fluor-benzylamino)-pyridin-maleat"
DE69320875T2 (de)	1999-04-08	Fumarsäuresalze von Chinolinderivaten zur Aufhebung von vielfacher Drogenresistenz in der Krebsbehandlung
EP0645390A1 (fr)	1995-03-29	Pyrimido 5,4-d pyrimidines trisubstitués pour moduler la résistance multidrogue, médicaments les contenant et procédés pour leur préparation
DE3447003C2 (de)	1994-11-17	7-Acylamino-9a-methoxymitosane, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Mittel
DD243285A5 (de)	1987-02-25	Verfahren zur herstellung kristallinen 7-(dimethylaminomethylen)-amino-9a-methoxymitosans
DE3217769A1 (de)	1982-12-09	Mitomycon-analoge verbindungen
AT396688B (de)	1993-11-25	Verfahren zur herstellung von kristallinem
AT394724B (de)	1992-06-10	Verfahren zur herstellung von n7-amidino-substituierten mitomycin-c-derivaten
AT392001B (de)	1991-01-10	Verfahren zum sterilen beschicken von phiolen mit 7-(dimethylaminomethylen)-amino-9a-methoxymitos n
DE3241764A1 (de)	1983-05-26	Neue azino-rifamycine
DE2430454A1 (de)	1976-01-15	Neue pyrazolo eckige klammer auf 3,4d eckige klammer zu pyrimidine
DE3851054T2 (de)	1995-03-09	Antitumor 6-sulfenamid, 6-sulfinamid und 6-sulfonamid-purine, purin-nukleoside, purin-nukleotide und verwandte verbindungen.
EP0113911B1 (fr)	1986-03-26	Pyrido-triazoloquinazolines, leur préparation et utilisation
DE2901537C2 (fr)	1988-10-27
DE69704840T2 (de)	2001-12-20	Ellipticinderivate, ihre Herstellung und diese enthaltende pharmazeutische Zubereitungen
AT397091B (de)	1994-01-25	Verfahren zur herstellung von neuen mitosan-derivaten
AT399339B (de)	1995-04-25	Verfahren zur herstellung von teilweise neuen substituierten 7-oxomitosanen