CS271331B2 - Method of mitomycin's n7-amidino-substituted derivatives production - Google Patents

Method of mitomycin's n7-amidino-substituted derivatives production Download PDF

Info

Publication number: CS271331B2
Authority: CS; Czechoslovakia
Prior art keywords: mitomycin; chloride; amino; reacted; methoxymitosan
Prior art date: 1985-04-29

Application number

CS863117A

Other languages

Czech (cs)

English (en)

Other versions

CS311786A2 (en

Inventor

Takushi Kaneko

Henry S L Wong

Original Assignee

Bristol Myers Squibb 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.)

1985-04-29

Filing date

1986-04-29

Publication date

1990-09-12

1986-04-29 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1989-12-13 Publication of CS311786A2 publication Critical patent/CS311786A2/cs

1990-09-12 Publication of CS271331B2 publication Critical patent/CS271331B2/cs

Links

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 title claims description 64
229960004857 mitomycin Drugs 0.000 title claims description 31
238000000034 method Methods 0.000 title claims description 16
229930192392 Mitomycin Natural products 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 12
-1 1-pyrrolidinylmethylene Chemical group 0.000 claims description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
150000003512 tertiary amines Chemical class 0.000 claims description 5
FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
239000003880 polar aprotic solvent Substances 0.000 claims description 3
AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
JYMQQKIMCZOSMX-UHFFFAOYSA-N thiomorpholine-4-carbaldehyde Chemical compound O=CN1CCSCC1 JYMQQKIMCZOSMX-UHFFFAOYSA-N 0.000 claims description 2
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
239000003245 coal Substances 0.000 claims 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 21
241000699670 Mus sp. Species 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 5
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
238000000855 fermentation Methods 0.000 description 4
230000004151 fermentation Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
HRHKSTOGXBBQCB-UHFFFAOYSA-N Mitomycin E Chemical class O=C1C(N)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)C3N(C)C3CN12 HRHKSTOGXBBQCB-UHFFFAOYSA-N 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
241000699666 Mus <mouse, genus> Species 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
230000000259 anti-tumor effect Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection 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
125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
230000004083 survival effect Effects 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
230000005595 deprotonation Effects 0.000 description 2
238000010537 deprotonation reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
150000003222 pyridines Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
206010052747 Adenocarcinoma pancreas Diseases 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
208000008342 Leukemia P388 Diseases 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
206010070863 Toxicity to various agents Diseases 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001409 amidines Chemical group 0.000 description 1
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000010171 animal model Methods 0.000 description 1
238000003556 assay Methods 0.000 description 1
125000004045 azirinyl group Chemical group 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
235000010633 broth Nutrition 0.000 description 1
239000000872 buffer Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000019365 chlortetracycline Nutrition 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
201000006585 gastric adenocarcinoma Diseases 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000005917 in vivo anti-tumor Effects 0.000 description 1
QMRIWYCCTCNABA-UHFFFAOYSA-N indole-4,7-quinone Chemical compound O=C1C=CC(=O)C2=C1C=CN2 QMRIWYCCTCNABA-UHFFFAOYSA-N 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
238000009533 lab test Methods 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
CHJQVUHGYWACSL-UHFFFAOYSA-N n,n-dimethylmethanimidamide;hydrochloride Chemical compound [Cl-].CN(C)C=[NH2+] CHJQVUHGYWACSL-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000009116 palliative therapy Methods 0.000 description 1
201000002094 pancreatic adenocarcinoma Diseases 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000013641 positive control Substances 0.000 description 1
230000003389 potentiating effect Effects 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/06—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing nitrogen as ring hetero atoms
- 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
- 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
- C07D487/02—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 two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

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

CS863117A 1985-04-29 1986-04-29 Method of mitomycin's n7-amidino-substituted derivatives production CS271331B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/728,650 US4652644A (en)	1985-04-29	1985-04-29	Process for preparation of N7 -amidino substituted mitomycin C derivatives

Publications (2)

Publication Number	Publication Date
CS311786A2 CS311786A2 (en)	1989-12-13
CS271331B2 true CS271331B2 (en)	1990-09-12

Family

ID=24927725

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS863117A CS271331B2 (en)	1985-04-29	1986-04-29	Method of mitomycin's n7-amidino-substituted derivatives production

Country Status (21)

Country	Link
US (1)	US4652644A (fr)
KR (1)	KR910002080B1 (fr)
CN (1)	CN1020731C (fr)
AR (1)	AR242210A1 (fr)
AT (1)	AT394724B (fr)
CA (1)	CA1247617A (fr)
CS (1)	CS271331B2 (fr)
DD (1)	DD258011A5 (fr)
DK (1)	DK168708B1 (fr)
ES (1)	ES8706685A1 (fr)
FI (1)	FI83519C (fr)
GR (1)	GR861152B (fr)
HU (1)	HU194243B (fr)
IT (1)	IT1208605B (fr)
LU (1)	LU86411A1 (fr)
NO (1)	NO164543C (fr)
OA (1)	OA08243A (fr)
PT (1)	PT82471B (fr)
SU (1)	SU1436881A3 (fr)
YU (1)	YU45778B (fr)
ZW (1)	ZW5386A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6354380A (ja) *	1986-08-26	1988-03-08	Kyowa Hakko Kogyo Co Ltd	マイトマイシン誘導体
JPH0867676A (ja) *	1994-03-30	1996-03-12	Eisai Kagaku Kk	保護アミノチアゾリル酢酸誘導体
JP3202960B2 (ja)	1998-02-17	2001-08-27	大塚化学株式会社	ハロゲン化剤及び水酸基のハロゲン化方法
CN104710426B (zh) *	2014-12-12	2017-08-01	常州大学	苯并吡咯里西啶生物碱及其制备方法和用途
CN104478885B (zh) *	2014-12-12	2017-08-01	常州大学	9‑氨基‑9a‑烯丙基苯并吡咯里西啶生物碱的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1135270B (it) *	1980-04-12	1986-08-20	Erba Farmitalia	3-amidino-ansamicine
US4487769A (en) *	1982-06-04	1984-12-11	Bristol-Myers Company	Amidines
US4567256A (en) *	1983-05-09	1986-01-28	Bristol-Myers Company	Amidine process

1985
- 1985-04-29 US US06/728,650 patent/US4652644A/en not_active Expired - Fee Related
1986
- 1986-02-11 CA CA000501609A patent/CA1247617A/fr not_active Expired
- 1986-02-28 KR KR1019860001449A patent/KR910002080B1/ko not_active Expired
- 1986-03-04 ZW ZW53/86A patent/ZW5386A1/xx unknown
- 1986-03-13 AR AR86303372A patent/AR242210A1/es active
- 1986-03-13 CN CN86101611A patent/CN1020731C/zh not_active Expired - Fee Related
- 1986-04-17 AT AT0101886A patent/AT394724B/de not_active IP Right Cessation
- 1986-04-24 FI FI861720A patent/FI83519C/fi not_active IP Right Cessation
- 1986-04-25 OA OA58844A patent/OA08243A/fr unknown
- 1986-04-28 PT PT82471A patent/PT82471B/pt not_active IP Right Cessation
- 1986-04-28 SU SU864027308A patent/SU1436881A3/ru active
- 1986-04-28 ES ES554469A patent/ES8706685A1/es not_active Expired
- 1986-04-28 LU LU86411A patent/LU86411A1/fr unknown
- 1986-04-28 NO NO861652A patent/NO164543C/no unknown
- 1986-04-28 DD DD86289675A patent/DD258011A5/de not_active IP Right Cessation
- 1986-04-28 IT IT8620228A patent/IT1208605B/it active
- 1986-04-28 DK DK193786A patent/DK168708B1/da not_active IP Right Cessation
- 1986-04-29 GR GR861152A patent/GR861152B/el unknown
- 1986-04-29 HU HU861783A patent/HU194243B/hu not_active IP Right Cessation
- 1986-04-29 CS CS863117A patent/CS271331B2/cs unknown
- 1986-04-29 YU YU70086A patent/YU45778B/sh unknown

Also Published As

Publication number	Publication date
KR910002080B1 (ko)	1991-04-03
HU194243B (en)	1988-01-28
SU1436881A3 (ru)	1988-11-07
KR860008201A (ko)	1986-11-12
DK193786A (da)	1986-10-30
OA08243A (fr)	1987-10-30
FI861720A0 (fi)	1986-04-24
AT394724B (de)	1992-06-10
ZW5386A1 (en)	1986-10-01
CN1020731C (zh)	1993-05-19
NO164543B (no)	1990-07-09
DK168708B1 (da)	1994-05-24
US4652644A (en)	1987-03-24
IT8620228A0 (it)	1986-04-28
GR861152B (en)	1986-09-02
NO861652L (no)	1986-10-30
DK193786D0 (da)	1986-04-28
ES8706685A1 (es)	1987-07-01
CS311786A2 (en)	1989-12-13
ES554469A0 (es)	1987-07-01
FI83519B (fi)	1991-04-15
DD258011A5 (de)	1988-07-06
FI83519C (fi)	1991-07-25
ATA101886A (de)	1991-11-15
LU86411A1 (fr)	1986-11-05
YU45778B (sh)	1992-07-20
CN86101611A (zh)	1986-12-17
IT1208605B (it)	1989-07-10
YU70086A (en)	1987-12-31
PT82471B (pt)	1988-10-14
FI861720A7 (fi)	1986-10-30
CA1247617A (fr)	1988-12-28
HUT40665A (en)	1987-01-28
PT82471A (en)	1986-05-01
AR242210A1 (es)	1993-03-31
NO164543C (no)	1990-10-17

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US5180722A (en)	1993-01-19	10,11-methylenedioxy-20(RS)-camptothecin and 10,11-methylenedioxy-20(S)-camptothecin analogs
SI9620103A (sl)	1998-10-31	Pirolopirimidini in postopki za njihovo pripravo
EP0418099A2 (fr)	1991-03-20	Analogue de la 10,11-méthylènedioxy-20(RS)camptothécine et de la 10,11-méthylènedioxy-20(S)-camptothécine
PT679656E (pt)	2001-12-28	Melhoramentos em complexos de platina
US4866180A (en)	1989-09-12	Amino disulfide thiol exchange products
EP2857402A1 (fr)	2015-04-08	Dérivé pyrrole[2,1-f][1,2,4]triazine et son effet antinéoplasique
US4487769A (en)	1984-12-11	Amidines
EP0305093B1 (fr)	1994-04-06	Dérivés de l'imidazo[1,2-b]pyridazine
NZ237363A (en)	1992-12-23	Imidazo(1,2-c)quinazoline derivatives, preparation and pharmaceutical compositions thereof
US4803212A (en)	1989-02-07	Amino disulfides
JP2006504632A (ja)	2006-02-09	チェックポイントキナーゼ（Ｗｅｅ１およびＣｈｋ１）の阻害剤
CS271331B2 (en)	1990-09-12	Method of mitomycin's n7-amidino-substituted derivatives production
EP0643699B1 (fr)	1996-10-23	6-(2-hydroxyethylaminoalkyl)-5,11-dioxo-5,6-dihydro-11h- indeno[1,2-c]isoquinoleines et leur utilisation comme agents anticancereux
EP3992191A1 (fr)	2022-05-04	Dérivés d'imidazo[4,5-c]quinoline et leur utilisation en tant qu'inhibiteurs de kinase atm
Antonini et al.	1995	Synthesis of (dialkylamino) alkyl-disubstituted pyrimido [5, 6, 1-de] acridines, a novel group of anticancer agents active on a multidrug resistant cell line
Jarman et al.	1993	Synthesis and cytotoxicity of potential tumor-inhibitory analogs of trimelamol (2, 4, 6-tris [(hydroxymethyl) methylamino]-1, 3, 5-triazine) having electron-withdrawing groups in place of methyl
WO1991004260A2 (fr)	1991-04-04	Analogues de 10,11-methylenedioxy-20(rs)-camptothecine et de 10,11-methylenedioxy-20(s)-camptothecine
Anderson et al.	1977	Pyridopyrimidines. 7. Ribonucleosides structurally related to the antitumor antibiotic sangivamycin
Schroeder et al.	1982	Synthesis and biological evaluation of 6-ethynyluracil, a thiol-specific alkylating pyrimidine
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US4691023A (en)	1987-09-01	Amino disulfides
US5374739A (en)	1994-12-20	Mitomycin analogs
US4720497A (en)	1988-01-19	6-purinyl N-/2-chloroethyl/carbamate and thiocarbamate and process for the preparation thereof
EP0485904B1 (fr)	1997-08-20	Dérivés de la mitomycine
US4853385A (en)	1989-08-01	7-N,8-N-Ethylenemitomycin 8-imines