NO329005B1 - Heksasykliske forbindelser, farmasoytiske preparater som omfatter forbindelsene, anvendelser av forbindelsene til fremstilling av medikamenter samt fremgangsmate for fremstilling av forbindelsene og fremgangsmater for fremstilling av mellomprodukter - Google Patents

Heksasykliske forbindelser, farmasoytiske preparater som omfatter forbindelsene, anvendelser av forbindelsene til fremstilling av medikamenter samt fremgangsmate for fremstilling av forbindelsene og fremgangsmater for fremstilling av mellomprodukter Download PDF

Info

Publication number: NO329005B1
Authority: NO; Norway
Prior art keywords: ethyl; pyrano; pyrido; indolizino; quinazoline
Prior art date: 2001-11-30

Application number

NO20042729A

Other languages

English (en)

Norwegian (no)

Other versions

NO20042729L (no

Inventor

Nobuo Shimma

Takeshi Murata

Satoshi Niizuma

Hitomi Suda

Masao Tsukazaki

Original Assignee

Chugai Pharmaceutical Co Ltd

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.)

2001-11-30

Filing date

2004-06-29

Publication date

2010-07-19

2004-06-29 Application filed by Chugai Pharmaceutical Co Ltd filed Critical Chugai Pharmaceutical Co Ltd

2004-08-27 Publication of NO20042729L publication Critical patent/NO20042729L/no

2010-07-19 Publication of NO329005B1 publication Critical patent/NO329005B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 312
238000002360 preparation method Methods 0.000 title claims description 126
238000000034 method Methods 0.000 title claims description 120
238000004519 manufacturing process Methods 0.000 title claims description 23
239000003814 drug Substances 0.000 title claims description 13
239000000543 intermediate Substances 0.000 title description 2
239000008194 pharmaceutical composition Substances 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 33
230000002062 proliferating effect Effects 0.000 claims abstract description 5
-1 hydroxy, amino Chemical group 0.000 claims description 107
VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 claims description 103
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 80
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 26
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 22
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
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229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
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QSQNDNKPPYNZJR-UHFFFAOYSA-N 1,3-dichloro-1,3,5-triazinane-2,4,6-trione hydrochloride Chemical compound Cl.Cln1c(=O)[nH]c(=O)n(Cl)c1=O QSQNDNKPPYNZJR-UHFFFAOYSA-N 0.000 claims description 16
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
201000011510 cancer Diseases 0.000 claims description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
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229940079593 drug Drugs 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
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239000011593 sulfur Chemical group 0.000 claims description 7
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125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
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125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
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125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
239000005864 Sulphur Substances 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
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238000007911 parenteral administration Methods 0.000 claims description 2
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238000005160 1H NMR spectroscopy Methods 0.000 description 162
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 114
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LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
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108091005981 phosphorylated proteins Proteins 0.000 description 1
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229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
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239000000651 prodrug Substances 0.000 description 1
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125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
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238000012552 review Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
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238000003345 scintillation counting Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000002356 single layer Substances 0.000 description 1
230000005783 single-strand break Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
VSIVTUIKYVGDCX-UHFFFAOYSA-M sodium;4-[2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)tetrazol-2-ium-5-yl]benzene-1,3-disulfonate Chemical compound [Na+].COC1=CC([N+]([O-])=O)=CC=C1[N+]1=NC(C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)=NN1C1=CC=C([N+]([O-])=O)C=C1 VSIVTUIKYVGDCX-UHFFFAOYSA-M 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
AHJWSRRHTXRLAQ-UHFFFAOYSA-N tetramethoxymethane Chemical compound COC(OC)(OC)OC AHJWSRRHTXRLAQ-UHFFFAOYSA-N 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

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

NO20042729A 2001-11-30 2004-06-29 Heksasykliske forbindelser, farmasoytiske preparater som omfatter forbindelsene, anvendelser av forbindelsene til fremstilling av medikamenter samt fremgangsmate for fremstilling av forbindelsene og fremgangsmater for fremstilling av mellomprodukter NO329005B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01128361		2001-11-30
PCT/EP2002/013216 WO2003045952A2 (en)	2001-11-30	2002-11-25	Condensed camptothecins as antitumor agents

Publications (2)

Publication Number	Publication Date
NO20042729L NO20042729L (no)	2004-08-27
NO329005B1 true NO329005B1 (no)	2010-07-19

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ID=8179394

Family Applications (1)

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NO20042729A NO329005B1 (no)	2001-11-30	2004-06-29	Heksasykliske forbindelser, farmasoytiske preparater som omfatter forbindelsene, anvendelser av forbindelsene til fremstilling av medikamenter samt fremgangsmate for fremstilling av forbindelsene og fremgangsmater for fremstilling av mellomprodukter

Country Status (28)

Country	Link
US (2)	US6825194B2 (pl)
EP (1)	EP1480984B9 (pl)
JP (1)	JP4305909B2 (pl)
KR (1)	KR100895746B1 (pl)
CN (1)	CN100338066C (pl)
AT (1)	ATE398131T1 (pl)
AU (1)	AU2002356720B2 (pl)
BR (1)	BR0214615A (pl)
CA (1)	CA2468824C (pl)
DE (1)	DE60227113D1 (pl)
ES (1)	ES2307830T3 (pl)
GT (1)	GT200200250A (pl)
HU (1)	HUP0500062A3 (pl)
IL (1)	IL162058A0 (pl)
MX (1)	MXPA04005185A (pl)
MY (1)	MY136138A (pl)
NO (1)	NO329005B1 (pl)
NZ (1)	NZ533568A (pl)
PA (1)	PA8558901A1 (pl)
PE (1)	PE20030725A1 (pl)
PL (1)	PL207510B1 (pl)
RS (1)	RS51051B (pl)
RU (1)	RU2299212C2 (pl)
TW (1)	TWI258481B (pl)
UA (1)	UA80409C2 (pl)
UY (1)	UY27560A1 (pl)
WO (1)	WO2003045952A2 (pl)
ZA (1)	ZA200404522B (pl)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2004073601A2 (en) *	2003-02-21	2004-09-02	Chugai Seiyaku Kabushiki Kaisha	Process for the preparation of hexacyclic camptothecin derivatives
UA88008C2 (en)	2004-04-09	2009-09-10	Чугей Сейяку Кабусики Кайся	Water-soluble prodrugs
TW200744603A (en) *	2005-08-22	2007-12-16	Chugai Pharmaceutical Co Ltd	Novel anticancer concomitant drug
KR20080066039A (ko) *	2005-10-19	2008-07-15	추가이 세이야쿠 가부시키가이샤	신규 수용성 프로드러그를 함유하는 췌장암, 난소암 또는 간암의 예방 또는 치료제
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2002
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Also Published As

Publication number	Publication date
KR100895746B1 (ko)	2009-04-30
BR0214615A (pt)	2004-09-14
RU2299212C2 (ru)	2007-05-20
PA8558901A1 (es)	2003-06-30
WO2003045952A3 (en)	2003-10-16
WO2003045952A2 (en)	2003-06-05
ES2307830T3 (es)	2008-12-01
PL370479A1 (pl)	2005-05-30
UY27560A1 (es)	2003-05-30
MY136138A (en)	2008-08-29
EP1480984B1 (en)	2008-06-11
PE20030725A1 (es)	2003-08-28
CN1617874A (zh)	2005-05-18
TW200408642A (en)	2004-06-01
JP4305909B2 (ja)	2009-07-29
CA2468824A1 (en)	2003-06-05
UA80409C2 (en)	2007-09-25
EP1480984B9 (en)	2009-03-11
US20050059679A1 (en)	2005-03-17
RS47004A (sr)	2007-02-05
MXPA04005185A (es)	2004-08-11
KR20040062976A (ko)	2004-07-09
EP1480984A2 (en)	2004-12-01
JP2005511643A (ja)	2005-04-28
CN100338066C (zh)	2007-09-19
PL207510B1 (pl)	2010-12-31
RS51051B (sr)	2010-10-31
US20030144304A1 (en)	2003-07-31
CA2468824C (en)	2011-01-11
ATE398131T1 (de)	2008-07-15
GT200200250A (es)	2004-01-15
NZ533568A (en)	2006-01-27
HK1072935A1 (en)	2005-09-16
NO20042729L (no)	2004-08-27
US6825194B2 (en)	2004-11-30
HK1077303A1 (en)	2006-02-10
ZA200404522B (en)	2005-01-04
AU2002356720B2 (en)	2009-01-29
IL162058A0 (en)	2005-11-20
US7109195B2 (en)	2006-09-19
DE60227113D1 (de)	2008-07-24
RU2004119841A (ru)	2005-03-27
HUP0500062A3 (en)	2012-12-28
TWI258481B (en)	2006-07-21
AU2002356720A1 (en)	2003-06-10
HUP0500062A2 (hu)	2005-04-28

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US6825194B2 (en)	2004-11-30	Hexacyclic compounds
AU2006305169A1 (en)	2007-04-26	Preventive or therapeutic agents for pancreatic cancer, ovarian cancer, or liver cancer comprising a novel water-soluble prodrug
HK1072935C (en)	2008-09-05	Hexacyclic compounds
HK1072935B (en)	2008-09-05	Hexacyclic compounds