NO313143B1 - Farnesyltransferase-inhiberende 1,8-annelerte kinolinonderivater substituert med N- eller C-bundede imidazoler - Google Patents

Farnesyltransferase-inhiberende 1,8-annelerte kinolinonderivater substituert med N- eller C-bundede imidazoler Download PDF

Info

Publication number: NO313143B1
Authority: NO; Norway
Prior art keywords: formula; hydrogen; chlorophenyl; compounds; halo
Prior art date: 1997-03-10

Application number

NO19994268A

Other languages

English (en)

Norwegian (no)

Other versions

NO994268D0 (no

NO994268L (no

Inventor

Marc Gaston Venet

Patrick Rene Angibaud

Yannick Aime Eddy Ligny

Virginie Sophie Poncelet

Gerard Charles Sanz

Original Assignee

Janssen Pharmaceutica Nv

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.)

1997-03-10

Filing date

1999-09-02

Publication date

2002-08-19

1999-09-02 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1999-09-02 Publication of NO994268D0 publication Critical patent/NO994268D0/no

1999-11-08 Publication of NO994268L publication Critical patent/NO994268L/no

2002-08-19 Publication of NO313143B1 publication Critical patent/NO313143B1/no

Links

108010007508 Farnesyltranstransferase Proteins 0.000 title abstract description 4
102000007317 Farnesyltranstransferase Human genes 0.000 title abstract description 4
230000002401 inhibitory effect Effects 0.000 title abstract description 4
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title description 5
150000002460 imidazoles Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 116
239000001257 hydrogen Substances 0.000 claims abstract description 57
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
150000002431 hydrogen Chemical class 0.000 claims abstract description 28
239000002253 acid Substances 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 20
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 17
238000002360 preparation method Methods 0.000 claims abstract description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
239000001301 oxygen Substances 0.000 claims abstract description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
229910052717 sulfur Chemical group 0.000 claims abstract description 5
239000011593 sulfur Chemical group 0.000 claims abstract description 5
239000003814 drug Substances 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
125000001475 halogen functional group Chemical group 0.000 claims abstract 12
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239000000543 intermediate Substances 0.000 claims description 98
150000003254 radicals Chemical class 0.000 claims description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 18
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238000000034 method Methods 0.000 claims description 12
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239000002585 base Substances 0.000 claims description 10
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238000012360 testing method Methods 0.000 description 20
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230000000694 effects Effects 0.000 description 12
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
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NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
NSCKJKWCNIQOSL-UHFFFAOYSA-N n-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)-hydroxy-(3-methylimidazol-4-yl)methyl]-2-methoxyquinolin-8-yl]acetamide Chemical compound C=12C=C(C(O)(C=3N(C=NC=3)C)C=3C=CC(Cl)=CC=3)C=C(NC(C)=O)C2=NC(OC)=CC=1C1=CC=CC(Cl)=C1 NSCKJKWCNIQOSL-UHFFFAOYSA-N 0.000 description 1
UTYNDXOUGVOHGV-UHFFFAOYSA-N n-[6-bromo-4-(3-chlorophenyl)-2-methoxyquinolin-8-yl]acetamide Chemical compound C=12C=C(Br)C=C(NC(C)=O)C2=NC(OC)=CC=1C1=CC=CC(Cl)=C1 UTYNDXOUGVOHGV-UHFFFAOYSA-N 0.000 description 1
CPKNOABHYZJYDC-UHFFFAOYSA-N n-[6-bromo-4-(3-chlorophenyl)-2-oxo-1h-quinolin-8-yl]acetamide Chemical compound C=1C(=O)NC=2C(NC(=O)C)=CC(Br)=CC=2C=1C1=CC=CC(Cl)=C1 CPKNOABHYZJYDC-UHFFFAOYSA-N 0.000 description 1
UIUBSDQUWWDYQK-UHFFFAOYSA-N n-acetyl-n-[2-(3-chlorobenzoyl)-4-(4-chlorobenzoyl)-6-methoxyphenyl]acetamide Chemical compound CC(=O)N(C(C)=O)C=1C(OC)=CC(C(=O)C=2C=CC(Cl)=CC=2)=CC=1C(=O)C1=CC=CC(Cl)=C1 UIUBSDQUWWDYQK-UHFFFAOYSA-N 0.000 description 1
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FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000003961 penetration enhancing agent Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 description 1
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CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
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GYESAYHWISMZOK-UHFFFAOYSA-N quinolin-5-ol Chemical compound C1=CC=C2C(O)=CC=CC2=N1 GYESAYHWISMZOK-UHFFFAOYSA-N 0.000 description 1
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239000012312 sodium hydride Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Cosmetics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO19994268A 1997-03-10 1999-09-02 Farnesyltransferase-inhiberende 1,8-annelerte kinolinonderivater substituert med N- eller C-bundede imidazoler NO313143B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP97200708		1997-03-10
EP97200709		1997-03-10
PCT/EP1998/001296 WO1998040383A1 (en)	1997-03-10	1998-03-03	Farnesyl transferase inhibiting 1,8-annelated quinolinone derivatives substituted with n- or c-linked imidazoles

Publications (3)

Publication Number	Publication Date
NO994268D0 NO994268D0 (no)	1999-09-02
NO994268L NO994268L (no)	1999-11-08
NO313143B1 true NO313143B1 (no)	2002-08-19

Family

ID=26146222

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19994268A NO313143B1 (no)	1997-03-10	1999-09-02	Farnesyltransferase-inhiberende 1,8-annelerte kinolinonderivater substituert med N- eller C-bundede imidazoler

Country Status (21)

Country	Link
US (2)	US6187786B1 (pl)
EP (1)	EP0970079B1 (pl)
JP (1)	JP4272262B2 (pl)
KR (1)	KR100549096B1 (pl)
CN (1)	CN1128797C (pl)
AT (1)	ATE251159T1 (pl)
AU (1)	AU748702B2 (pl)
BR (1)	BR9808843A (pl)
CA (1)	CA2283587C (pl)
DE (1)	DE69818649T2 (pl)
ES (1)	ES2209127T3 (pl)
HU (1)	HUP0001498A3 (pl)
IL (1)	IL130362A (pl)
NO (1)	NO313143B1 (pl)
NZ (1)	NZ336234A (pl)
PL (1)	PL191564B1 (pl)
RU (1)	RU2204553C2 (pl)
SK (1)	SK283927B6 (pl)
TR (1)	TR199902203T2 (pl)
TW (1)	TW591030B (pl)
WO (1)	WO1998040383A1 (pl)

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EP1097150B1 (en) *	1998-06-16	2004-03-24	Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S.	Imidazolyl derivatives
HRP20000904A2 (en)	1998-07-06	2001-12-31	Janssen Pharmaceutica Nv	Farnesyl protein transferase inhibitors for treating arthropathies
ID26987A (id)	1998-07-06	2001-02-22	Janssen Pharmaceutica Nv	Inhibitor-inhibitor transferase protein farnesil dengan sifat-sifat peka terhadap sinar radiasi in vivo
CA2341739C (en) *	1998-08-27	2005-07-12	Pfizer Products Inc.	Quinolin-2-one derivatives useful as anticancer agents
WO2000034239A2 (en)	1998-12-08	2000-06-15	Merck & Co., Inc.	Inhibitors of prenyl-protein transferase
AU2477400A (en)	1998-12-08	2000-06-26	Merck & Co., Inc.	Inhibitors of prenyl-protein transferase
PT1140935E (pt)	1998-12-23	2003-10-31	Janssen Pharmaceutica Nv	Derivados da quinolina 1,2-ciclizada
US6143766A (en) *	1999-04-16	2000-11-07	Warner-Lambert Company	Benzopyranone and quinolone inhibitors of ras farnesyl transferase
EP1420015A1 (en) *	1999-06-11	2004-05-19	Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S.	Imidazolyl derivatives
DE19950647A1 (de) *	1999-10-21	2001-04-26	Merck Patent Gmbh	Imidazolderivate als Phosphodiesterase VII-Hemmer
JP4883862B2 (ja)	1999-11-15	2012-02-22	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	ファルネシルトランスフェラーゼ阻害剤としてのトリアゾール類
ES2212971T3 (es)	1999-11-30	2004-08-16	Pfizer Products Inc.	Derivados de quinolina utiles para la inhibicion de la farnesil protein transferasa.
KR20010077400A (ko) *	2000-02-02	2001-08-17	성재갑	에프타아제 저해제인 엘비42908과 타(他) 항암제와의조합에 의한 항암치료제
PT1255537E (pt) *	2000-02-04	2006-09-29	Janssen Pharmaceutica Nv	Inibidores da proteina farnesil transferase para tratar cancro da mama
JP2003523381A (ja)	2000-02-24	2003-08-05	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	投与レジメン
WO2001064217A2 (en) *	2000-02-29	2001-09-07	Janssen Pharmaceutica N.V.	Combinations of a farnesyl protein transferase inhibitor with nitrogen mustard or nitrosourea alkylating agents
AU2001244166A1 (en) *	2000-02-29	2001-09-12	Janssen Pharmaceutica N.V.	Farnesyl protein transferase inhibitor combinations with further anti-cancer agents
CA2397256A1 (en) *	2000-02-29	2001-09-07	Mary Ellen Margaret Rybak	Farnesyl protein transferase inhibitor combinations with anti-tumor podophyllotoxin derivatives
CA2397690A1 (en) *	2000-02-29	2001-09-07	Janssen Pharmaceutica N.V.	Farnesyl protein transferase inhibitor combinations with anti-tumor nucleoside derivatives
US20030181473A1 (en) *	2000-02-29	2003-09-25	Palmer Peter Albert	Farnesyl protein transferase inhibitor combinations with taxane compounds
AU2001246477A1 (en) *	2000-02-29	2001-09-12	Janssen Pharmaceutica N.V.	Farnesyl protein transferase inhibitor combinations with platinum compounds
AU2001242434A1 (en) *	2000-02-29	2001-09-12	Janssen Pharmaceutica N.V.	Farnesyl protein transferase inhibitor combinations with vinca alkaloids
CA2397349A1 (en) *	2000-02-29	2001-09-07	Ivan David Horak	Farnesyl protein transferase inhibitor combinations with an her2 antibody
AU2001240658A1 (en) *	2000-02-29	2001-09-12	Janssen Pharmaceutica N.V.	Farnesyl protein transferase inhibitor combinations with camptothecin compounds
JP2003525237A (ja) *	2000-02-29	2003-08-26	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	抗腫瘍性アントラサイクリン誘導体とのファルネシルタンパク質トランスフェラーゼ阻害剤組み合わせ剤
AU2001252147A1 (en) *	2000-02-29	2001-09-12	Janssen Pharmaceutica N.V.	Farnesyl protein transferase inhibitor combinations
JO2361B1 (en) *	2000-06-22	2006-12-12	جانسين فارماسيوتيكا ان. في	Enaniumer 1,2-anylated quinoline inhibitor for the transporter - farnesyl
US6881842B2 (en)	2000-09-21	2005-04-19	Takeda Chemical Industries, Ltd.	Process for producing tricyclic fused heterocyclic derivative
WO2002024683A1 (en) *	2000-09-25	2002-03-28	Janssen Pharmaceutica N.V.	Farnesyl transferase inhibiting 6-[(substituted phenyl)methyl]-quinoline and quinazoline derivatives
US7053105B2 (en)	2000-09-25	2006-05-30	Janssen Pharmaceutica, N.V.	Farnesyl transferase inhibiting quinoline and quinazoline derivatives as farnesyl transferase inhibitors
JP4974439B2 (ja)	2000-09-25	2012-07-11	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	ファルネシルトランスフェラーゼを阻害する６−ヘテロシクリルメチルキノリノン誘導体
ATE409189T1 (de)	2000-09-25	2008-10-15	Janssen Pharmaceutica Nv	Farnesyl transferase-hemmende 6- heterocyclylmethyl-chinolin und chinazol-derivate
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Publication number	Publication date
CN1249753A (zh)	2000-04-05
BR9808843A (pt)	2000-07-04
HUP0001498A2 (hu)	2000-11-28
SK121799A3 (en)	2000-05-16
PL335518A1 (en)	2000-04-25
IL130362A (en)	2004-02-19
CA2283587A1 (en)	1998-09-17
ES2209127T3 (es)	2004-06-16
TW591030B (en)	2004-06-11
AU7031898A (en)	1998-09-29
TR199902203T2 (xx)	1999-12-21
NZ336234A (en)	2000-10-27
JP2001515487A (ja)	2001-09-18
DE69818649T2 (de)	2004-07-01
DE69818649D1 (de)	2003-11-06
IL130362A0 (en)	2000-06-01
US20020049327A1 (en)	2002-04-25
NO994268D0 (no)	1999-09-02
NO994268L (no)	1999-11-08
KR20000069559A (ko)	2000-11-25
JP4272262B2 (ja)	2009-06-03
SK283927B6 (sk)	2004-05-04
EP0970079A1 (en)	2000-01-12
KR100549096B1 (ko)	2006-02-06
RU2204553C2 (ru)	2003-05-20
US6187786B1 (en)	2001-02-13
PL191564B1 (pl)	2006-06-30
HUP0001498A3 (en)	2001-01-29
CN1128797C (zh)	2003-11-26
AU748702B2 (en)	2002-06-13
ATE251159T1 (de)	2003-10-15
CA2283587C (en)	2007-05-01
US6444812B1 (en)	2002-09-03
WO1998040383A1 (en)	1998-09-17
EP0970079B1 (en)	2003-10-01
HK1024689A1 (en)	2000-10-20

Publication	Publication Date	Title
EP0970079B1 (en)	2003-10-01	Farnesyl transferase inhibiting 1,8-annelated quinolinone derivatives substituted with n- or c-linked imidazoles
US6458800B1 (en)	2002-10-01	1,2-annelated quinoline derivatives
NO317576B1 (no)	2004-11-15	Farnesyltransferase-inhiberende quinazolinoner
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NO314037B1 (no)	2003-01-20	Farnesyltransferase-inhiberende 2-kinolonderivater
US7153958B2 (en)	2006-12-26	Farnesyl transferase inhibiting benzoheterocyclic derivatives
HK1024689B (en)	2004-03-05	Farnesyl transferase inhibiting 1,8-annelated quinolinone derivatives substituted with n- or c-linked imidazoles
CZ316799A3 (cs)	2000-03-15	1,8-Anelované chinolinonové deriváty substituované N- nebo C-vázanými imidazoly inhibující farnesyl transferázu
MXPA01006614A (en)	2002-03-26	1,2-annelated quinoline derivatives
MXPA99009763A (en)	2000-09-04	Farnesyltransferase inhibiting quinazolinones