NL8600455A - Werkwijze voor het in flesjes deponeren van 7-(dimethylaminomethyleen) amino-9a-methoxymitosaan. - Google Patents

Werkwijze voor het in flesjes deponeren van 7-(dimethylaminomethyleen) amino-9a-methoxymitosaan. Download PDF

Info

Publication number: NL8600455A
Authority: NL; Netherlands
Prior art keywords: amino; methoxymitosane; tertiary butanol; dimethylaminomethylene; solution
Prior art date: 1985-02-25

Application number

NL8600455A

Other languages

English (en)

Dutch (nl)

Original Assignee

Bristol Myers Co

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.)

1985-02-25

Filing date

1986-02-24

Publication date

1986-09-16

1986-02-24 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1986-09-16 Publication of NL8600455A publication Critical patent/NL8600455A/nl

Links

-1 DIMETHYLAMINOMETHYLENE Chemical class 0.000 title claims description 31
238000000034 method Methods 0.000 title claims description 22
238000000151 deposition Methods 0.000 title claims description 5
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 28
239000000243 solution Substances 0.000 claims description 26
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 12
238000001704 evaporation Methods 0.000 claims description 6
230000008020 evaporation Effects 0.000 claims description 6
229960003966 nicotinamide Drugs 0.000 claims description 6
235000005152 nicotinamide Nutrition 0.000 claims description 6
239000011570 nicotinamide Substances 0.000 claims description 6
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 4
238000004108 freeze drying Methods 0.000 claims description 4
239000007979 citrate buffer Substances 0.000 claims description 2
229960004295 valine Drugs 0.000 claims 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 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
150000001875 compounds Chemical class 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
229960004857 mitomycin Drugs 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
230000000694 effects Effects 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000003981 vehicle Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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 4
238000000855 fermentation Methods 0.000 description 4
230000004151 fermentation Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
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 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000004809 thin layer chromatography Methods 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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
229930192392 Mitomycin Natural products 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000007864 aqueous solution Substances 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
239000002552 dosage form Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000003756 stirring 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
241001529936 Murinae Species 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
SEZWJRWTCIPRSV-UHFFFAOYSA-N [N]C(N)=O Chemical group [N]C(N)=O SEZWJRWTCIPRSV-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229920005549 butyl rubber Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
235000019365 chlortetracycline Nutrition 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
238000006073 displacement reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
201000006585 gastric adenocarcinoma Diseases 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
231100000086 high toxicity Toxicity 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000001394 metastastic effect Effects 0.000 description 1
206010061289 metastatic neoplasm Diseases 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
238000002156 mixing Methods 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000002638 palliative care Methods 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
201000002094 pancreatic adenocarcinoma Diseases 0.000 description 1
229920001993 poloxamer 188 Polymers 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 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
238000002560 therapeutic procedure Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Medicinal Preparation (AREA)

NL8600455A 1985-02-25 1986-02-24 Werkwijze voor het in flesjes deponeren van 7-(dimethylaminomethyleen) amino-9a-methoxymitosaan. NL8600455A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US70524385A	1985-02-25	1985-02-25
US70524385		1985-02-25

Publications (1)

Publication Number	Publication Date
NL8600455A true NL8600455A (nl)	1986-09-16

Family

ID=24832630

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8600455A NL8600455A (nl)	1985-02-25	1986-02-24	Werkwijze voor het in flesjes deponeren van 7-(dimethylaminomethyleen) amino-9a-methoxymitosaan.

Country Status (29)

Country	Link
US (1)	US4792566A (fr)
JP (1)	JPS61246125A (fr)
KR (1)	KR860006267A (fr)
CN (1)	CN1011289B (fr)
AT (1)	AT392001B (fr)
AU (1)	AU593786B2 (fr)
BE (1)	BE904272A (fr)
CA (1)	CA1262097A (fr)
CH (1)	CH670387A5 (fr)
DD (1)	DD243207A5 (fr)
DE (1)	DE3605888A1 (fr)
DK (1)	DK166307C (fr)
ES (1)	ES8705233A1 (fr)
FI (1)	FI83038C (fr)
FR (1)	FR2581870B1 (fr)
GB (1)	GB2171408B (fr)
GR (1)	GR860534B (fr)
HU (1)	HU193850B (fr)
IT (1)	IT1188708B (fr)
LU (1)	LU86320A1 (fr)
MY (1)	MY102923A (fr)
NL (1)	NL8600455A (fr)
NO (1)	NO169323C (fr)
NZ (1)	NZ215122A (fr)
OA (1)	OA08211A (fr)
PT (1)	PT82078B (fr)
SE (1)	SE8600830L (fr)
YU (1)	YU45304B (fr)
ZA (1)	ZA86308B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5216011A (en) *	1989-09-01	1993-06-01	Bristol-Myers Squibb Co.	Stable solutions of mitomycin c
LT3272361T (lt)	2013-10-22	2020-01-10	Medac Gesellschaft für klinische Spezialpräparate mbH	Liofilizuotos farmacinės kompozicijos, kurioje yra mitomicino c, gamybos būdas

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3660578A (en) *	1957-04-06	1972-05-02	Kyowa Hakko Kogyo Kk	Mitomycin c
ZA833967B (en) *	1982-06-04	1984-02-29	Bristol Myers Co	Amidines
US4487769A (en) *	1982-06-04	1984-12-11	Bristol-Myers Company	Amidines
JPS60255789A (ja) *	1984-06-01	1985-12-17	Kyowa Hakko Kogyo Co Ltd	マイトマイシン誘導体，その製造法および抗腫瘍剤
US4639528A (en) *	1985-02-21	1987-01-27	Bristol-Myers Company	Crystalline form of 7-(dimethylaminomethylene-amino-9a-methoxymitosane
DE3674043D1 (de) *	1985-04-10	1990-10-18	Kyowa Hakko Kogyo Kk	Pharmakologisch aktive mitomycinderivate.

1986
- 1986-01-15 ZA ZA86308A patent/ZA86308B/xx unknown
- 1986-02-11 FR FR868601816A patent/FR2581870B1/fr not_active Expired
- 1986-02-12 JP JP61028744A patent/JPS61246125A/ja active Pending
- 1986-02-14 CN CN86100997A patent/CN1011289B/zh not_active Expired
- 1986-02-18 AU AU53684/86A patent/AU593786B2/en not_active Ceased
- 1986-02-19 FI FI860735A patent/FI83038C/fi not_active IP Right Cessation
- 1986-02-20 YU YU259/86A patent/YU45304B/xx unknown
- 1986-02-21 CA CA000502443A patent/CA1262097A/fr not_active Expired
- 1986-02-21 NZ NZ215122A patent/NZ215122A/xx unknown
- 1986-02-21 IT IT19493/86A patent/IT1188708B/it active
- 1986-02-24 DK DK085486A patent/DK166307C/da not_active IP Right Cessation
- 1986-02-24 PT PT82078A patent/PT82078B/pt not_active IP Right Cessation
- 1986-02-24 NO NO860668A patent/NO169323C/no unknown
- 1986-02-24 KR KR1019860001281A patent/KR860006267A/ko not_active Ceased
- 1986-02-24 DD DD86287290A patent/DD243207A5/de not_active IP Right Cessation
- 1986-02-24 SE SE8600830A patent/SE8600830L/xx not_active Application Discontinuation
- 1986-02-24 ES ES552323A patent/ES8705233A1/es not_active Expired
- 1986-02-24 DE DE19863605888 patent/DE3605888A1/de not_active Ceased
- 1986-02-24 LU LU86320A patent/LU86320A1/fr unknown
- 1986-02-24 GB GB08604514A patent/GB2171408B/en not_active Expired
- 1986-02-24 CH CH721/86A patent/CH670387A5/de not_active IP Right Cessation
- 1986-02-24 OA OA58793A patent/OA08211A/fr unknown
- 1986-02-24 NL NL8600455A patent/NL8600455A/nl not_active Application Discontinuation
- 1986-02-24 BE BE0/216303A patent/BE904272A/fr not_active IP Right Cessation
- 1986-02-25 HU HU86796A patent/HU193850B/hu not_active IP Right Cessation
- 1986-02-25 GR GR860534A patent/GR860534B/el unknown
- 1986-02-25 AT AT0049686A patent/AT392001B/de not_active IP Right Cessation
- 1986-05-14 US US06/863,202 patent/US4792566A/en not_active Expired - Fee Related
1987
- 1987-09-29 MY MYPI87002223A patent/MY102923A/en unknown

Also Published As

Publication number	Publication date
FI83038B (fi)	1991-02-15
CN86100997A (zh)	1986-10-22
NO169323B (no)	1992-03-02
FI860735A0 (fi)	1986-02-19
FR2581870B1 (fr)	1989-03-03
NZ215122A (en)	1989-06-28
FI83038C (fi)	1991-05-27
DK85486D0 (da)	1986-02-24
CA1262097A (fr)	1989-10-03
AT392001B (de)	1991-01-10
ZA86308B (en)	1986-11-26
DK166307B (da)	1993-04-05
JPS61246125A (ja)	1986-11-01
YU45304B (en)	1992-05-28
FR2581870A1 (fr)	1986-11-21
KR860006267A (ko)	1986-09-09
SE8600830L (sv)	1986-08-26
ES8705233A1 (es)	1987-05-01
GB2171408B (en)	1988-07-13
HUT40327A (en)	1986-12-28
NO860668L (no)	1986-08-26
YU25986A (en)	1987-12-31
HU193850B (en)	1987-12-28
MY102923A (en)	1993-03-31
SE8600830D0 (sv)	1986-02-24
ATA49686A (de)	1990-07-15
LU86320A1 (fr)	1986-09-02
DD243207A5 (de)	1987-02-25
GB2171408A (en)	1986-08-28
GB8604514D0 (en)	1986-04-03
CH670387A5 (fr)	1989-06-15
GR860534B (en)	1986-06-24
AU5368486A (en)	1986-08-28
PT82078A (en)	1986-03-01
DE3605888A1 (de)	1986-08-28
AU593786B2 (en)	1990-02-22
NO169323C (no)	1992-06-10
CN1011289B (zh)	1991-01-23
FI860735L (fi)	1986-08-26
DK166307C (da)	1993-08-23
IT1188708B (it)	1988-01-28
OA08211A (fr)	1987-10-30
ES552323A0 (es)	1987-05-01
DK85486A (da)	1986-08-26
PT82078B (pt)	1988-07-01
IT8619493A0 (it)	1986-02-21
US4792566A (en)	1988-12-20
BE904272A (fr)	1986-08-25

Legal Events

Date	Code	Title	Description
1990-05-16	DNT	Communications of changes of names of applicants whose applications have been laid open to public inspection	Free format text: BRISTOL-MYERS SQUIBB COMPANY
1993-03-01	BA	A request for search or an international-type search has been filed
1993-04-01	BB	A search report has been drawn up
1993-08-02	BC	A request for examination has been filed
1994-10-03	BV	The patent application has lapsed

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CA1337523C (fr)	1995-11-07	Acides pyridonecarboxyliques et agents antibacteriens
US12122783B2 (en)	2024-10-22	Stable salt of 5,10-methylene-(6R)-tetrahydrofolic acid
JPH02502462A (ja)	1990-08-09	化合物
KR100717489B1 (ko)	2007-05-14	피리도피리미디논 화합물, 이의 제조 방법 및 이를함유하는 약제 조성물
EA000897B1 (ru)	2000-06-26	ПРОИЗВОДНЫЕ ПИРИДО[2,3-d]ПИРИМИДИНА И ИХ ФАРМАЦЕВТИЧЕСКИ ПРИЕМЛЕМЫЕ СОЛИ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, ОБЛАДАЮЩАЯ ИНГИБИРУЮЩЕЙ ПРОТЕИН-ТИРОЗИН-КИНАЗУ АКТИВНОСТЬЮ, СПОСОБ ЛЕЧЕНИЯ ЗАБОЛЕВАНИЙ, ОПОСРЕДОВАННЫХ КЛЕТОЧНОЙ ПРОЛИФЕРАЦИЕЙ, И СПОСОБ ЛЕЧЕНИЯ РАКА, АТЕРОСКЛЕРОЗА, ПСОРИАЗА ИЛИ РЕСТЕНОЗА
JPH07107066B2 (ja)	1995-11-15	置換インドキノキサリン類
HU215967B (hu)	1999-03-29	Eljárás 6,9-bisz(helyettesített amino)-benzo[g]izokinolin-5,10-dion-származékok és e vegyületeket hatóanyagként tartalmazó gyógyászati készítmények előállítására
US6235751B1 (en)	2001-05-22	Quinolizine carboxylic acid derivatives
CS232000B2 (en)	1985-01-16	Manufacturing process of new ergoline derovatives
FI81099B (fi)	1990-05-31	Foerfarande foer framstaellning av terapeutiskt aktiva mitomycinanaloger.
EP0575890A1 (fr)	1993-12-29	Sels d'acide fumarique de dérivés de quinoléine pour surmonter la résistance multidrogne dans le traitement de cancer
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