NO314036B1 - Farnesylproteintransferase-inhiberende (imidazol-5-yl)metyl-2- kinolinonderivater - Google Patents

Farnesylproteintransferase-inhiberende (imidazol-5-yl)metyl-2- kinolinonderivater Download PDF

Info

Publication number: NO314036B1
Authority: NO; Norway
Prior art keywords: formula; methyl; 6alkyl; hydrogen; chlorophenyl
Prior art date: 1995-12-08

Application number

NO19980927A

Other languages

English (en)

Norwegian (no)

Other versions

NO980927D0 (no

NO980927L (no

Inventor

Marc Gaston Venet

Patrick Rene Angibaud

Philippe Muller

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.)

1995-12-08

Filing date

1998-03-04

Publication date

2003-01-20

1998-03-04 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1998-03-04 Publication of NO980927D0 publication Critical patent/NO980927D0/no

1998-06-08 Publication of NO980927L publication Critical patent/NO980927L/no

2003-01-20 Publication of NO314036B1 publication Critical patent/NO314036B1/no

Links

230000002401 inhibitory effect Effects 0.000 title claims description 7
108090000992 Transferases Proteins 0.000 title description 12
102000004357 Transferases Human genes 0.000 title description 12
125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 title description 12
AVGQUILLCRPWKH-UHFFFAOYSA-N 4-(1h-imidazol-5-yl)-3-methyl-1h-quinolin-2-one Chemical class C12=CC=CC=C2NC(=O)C(C)=C1C1=CN=CN1 AVGQUILLCRPWKH-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 165
239000001257 hydrogen Substances 0.000 claims description 69
229910052739 hydrogen Inorganic materials 0.000 claims description 69
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 58
239000000243 solution Substances 0.000 claims description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
239000002904 solvent Substances 0.000 claims description 45
150000002431 hydrogen Chemical class 0.000 claims description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
-1 4,4-dimethyloxazolyl Chemical group 0.000 claims description 39
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
239000002585 base Substances 0.000 claims description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 26
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 22
238000000034 method Methods 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000003153 chemical reaction reagent Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000002883 imidazolyl group Chemical group 0.000 claims description 8
150000001413 amino acids Chemical class 0.000 claims description 7
230000010261 cell growth Effects 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
150000003973 alkyl amines Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
150000002576 ketones Chemical class 0.000 claims description 5
125000004951 trihalomethoxy group Chemical group 0.000 claims description 5
230000004614 tumor growth Effects 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
230000002159 abnormal effect Effects 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000004953 trihalomethyl group Chemical group 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
229910010062 TiCl3 Inorganic materials 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
229910052717 sulfur Chemical group 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 claims description 3
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
239000003929 acidic solution Substances 0.000 claims description 2
238000007259 addition reaction Methods 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
238000003786 synthesis reaction Methods 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 5
ZMLMGCPNMBRTKN-UHFFFAOYSA-N 6-[(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-ethoxyphenyl)-1-methylquinolin-2-one;hydrate;hydrochloride Chemical compound O.Cl.CCOC1=CC=CC(C=2C3=CC(=CC=C3N(C)C(=O)C=2)C(C=2N(C=NC=2)C)C=2C=CC(Cl)=CC=2)=C1 ZMLMGCPNMBRTKN-UHFFFAOYSA-N 0.000 claims 1
PLHJCIYEEKOWNM-UHFFFAOYSA-N 6-[amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one Chemical compound CN1C=NC=C1C(N)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(C)C2=CC=1)C1=CC=C(Cl)C=C1 PLHJCIYEEKOWNM-UHFFFAOYSA-N 0.000 claims 1
230000003287 optical effect Effects 0.000 claims 1
229960005235 piperonyl butoxide Drugs 0.000 claims 1
230000002062 proliferating effect Effects 0.000 claims 1
230000001131 transforming effect Effects 0.000 claims 1
239000000203 mixture Substances 0.000 description 104
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 82
239000000543 intermediate Substances 0.000 description 73
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
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239000002244 precipitate Substances 0.000 description 29
239000012044 organic layer Substances 0.000 description 28
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239000003480 eluent Substances 0.000 description 26
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239000000741 silica gel Substances 0.000 description 23
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238000004440 column chromatography Methods 0.000 description 21
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
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238000012360 testing method Methods 0.000 description 18
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238000006243 chemical reaction Methods 0.000 description 17
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 16
235000011114 ammonium hydroxide Nutrition 0.000 description 16
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
150000003254 radicals Chemical class 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
108700042226 ras Genes Proteins 0.000 description 14
125000005843 halogen group Chemical group 0.000 description 13
108010014186 ras Proteins Proteins 0.000 description 13
102000016914 ras Proteins Human genes 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
108010037444 diisopropylglutathione ester Proteins 0.000 description 10
238000000746 purification Methods 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
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HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 9
231100000590 oncogenic Toxicity 0.000 description 9
230000002246 oncogenic effect Effects 0.000 description 9
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 9
230000009466 transformation Effects 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
229930185107 quinolinone Natural products 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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235000001014 amino acid Nutrition 0.000 description 6
229940024606 amino acid Drugs 0.000 description 6
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125000004432 carbon atom Chemical group C* 0.000 description 6
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
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239000003528 protein farnesyltransferase inhibitor Substances 0.000 description 4
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201000009410 rhabdomyosarcoma Diseases 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000002821 scintillation proximity assay Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
239000002356 single layer Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
230000008685 targeting Effects 0.000 description 1
208000001608 teratocarcinoma Diseases 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
239000003558 transferase inhibitor Substances 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000004565 tumor cell growth Effects 0.000 description 1
231100000588 tumorigenic Toxicity 0.000 description 1
230000000381 tumorigenic effect Effects 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
208000010570 urinary bladder carcinoma Diseases 0.000 description 1
239000004474 valine Substances 0.000 description 1
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238000010626 work up procedure Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO19980927A 1995-12-08 1998-03-04 Farnesylproteintransferase-inhiberende (imidazol-5-yl)metyl-2- kinolinonderivater NO314036B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP95203427		1995-12-08
PCT/EP1996/004515 WO1997021701A1 (en)	1995-12-08	1996-10-16	Farnesyl protein transferase inhibiting (imidazol-5-yl)methyl-2-quinolinone derivatives

Publications (3)

Publication Number	Publication Date
NO980927D0 NO980927D0 (no)	1998-03-04
NO980927L NO980927L (no)	1998-06-08
NO314036B1 true NO314036B1 (no)	2003-01-20

Family

ID=8220926

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19980927A NO314036B1 (no)	1995-12-08	1998-03-04	Farnesylproteintransferase-inhiberende (imidazol-5-yl)metyl-2- kinolinonderivater

Country Status (36)

Country	Link
US (3)	US6037350A (de)
EP (2)	EP0865440B1 (de)
JP (1)	JP3257559B2 (de)
KR (1)	KR100272676B1 (de)
CN (1)	CN1101392C (de)
AP (1)	AP1108A (de)
AR (1)	AR004992A1 (de)
AT (2)	ATE215541T1 (de)
AU (1)	AU711142B2 (de)
BG (1)	BG62615B1 (de)
BR (1)	BR9610745A (de)
CA (1)	CA2231105C (de)
CY (1)	CY2289B1 (de)
CZ (1)	CZ293296B6 (de)
DE (2)	DE69620445T2 (de)
DK (2)	DK1162201T3 (de)
EA (1)	EA000710B1 (de)
EE (1)	EE03484B1 (de)
ES (2)	ES2175137T3 (de)
HK (1)	HK1042482B (de)
HR (1)	HRP960576B1 (de)
HU (1)	HU221227B1 (de)
IL (1)	IL123568A (de)
MX (1)	MX9802068A (de)
MY (1)	MY114444A (de)
NO (1)	NO314036B1 (de)
NZ (1)	NZ320244A (de)
PL (1)	PL184171B1 (de)
PT (2)	PT1162201E (de)
SI (2)	SI0865440T1 (de)
SK (1)	SK283335B6 (de)
TR (1)	TR199800825T2 (de)
TW (1)	TW494101B (de)
UA (1)	UA57717C2 (de)
WO (1)	WO1997021701A1 (de)
ZA (1)	ZA9610254B (de)

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1996
- 1996-10-16 DE DE69620445T patent/DE69620445T2/de not_active Expired - Lifetime
- 1996-10-16 DK DK01202750T patent/DK1162201T3/da active
- 1996-10-16 PL PL96325962A patent/PL184171B1/pl unknown
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- 1996-10-16 SI SI9630477T patent/SI0865440T1/xx unknown
- 1996-10-16 UA UA98052686A patent/UA57717C2/uk unknown
- 1996-10-16 CN CN96198750A patent/CN1101392C/zh not_active Expired - Lifetime
- 1996-10-16 AT AT96934727T patent/ATE215541T1/de active
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- 1996-10-16 HU HU9900185A patent/HU221227B1/hu unknown
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2000
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Publication number	Publication date
DE69635966T2 (de)	2006-11-30
HU221227B1 (en)	2002-08-28
HUP9900185A2 (hu)	1999-04-28
TW494101B (en)	2002-07-11
AU711142B2 (en)	1999-10-07
HRP960576B1 (en)	2002-04-30
WO1997021701A1 (en)	1997-06-19
EE9800146A (et)	1998-10-15
NZ320244A (en)	1999-06-29
EP1162201A3 (de)	2003-11-26
KR100272676B1 (ko)	2000-11-15
HK1042482B (en)	2006-06-09
HK1012188A1 (en)	1999-07-30
CN1101392C (zh)	2003-02-12
US6169096B1 (en)	2001-01-02
PL184171B1 (pl)	2002-09-30
CA2231105A1 (en)	1997-06-19
PL325962A1 (en)	1998-08-17
NO980927D0 (no)	1998-03-04
ATE321757T1 (de)	2006-04-15
DE69635966D1 (de)	2006-05-18
PT865440E (pt)	2002-09-30
AP1108A (en)	2002-10-02
TR199800825T2 (xx)	1998-08-21
DK1162201T3 (da)	2006-07-17
ATE215541T1 (de)	2002-04-15
EP1162201A9 (de)	2002-04-03
US6420387B1 (en)	2002-07-16
EP0865440A1 (de)	1998-09-23
BG62615B1 (en)	2000-03-31
CN1203598A (zh)	1998-12-30
IL123568A0 (en)	1998-10-30
EP1162201B1 (de)	2006-03-29
EP1162201A2 (de)	2001-12-12
CY2289B1 (en)	2003-07-04
MY114444A (en)	2002-10-31
MX9802068A (es)	1998-08-30
AU7294896A (en)	1997-07-03
CZ293296B6 (cs)	2004-03-17
EP0865440B1 (de)	2002-04-03
EA000710B1 (ru)	2000-02-28
US6037350A (en)	2000-03-14
EA199800443A1 (ru)	1998-10-29
AP9801257A0 (en)	1998-06-30
SI0865440T1 (en)	2002-08-31
IL123568A (en)	2001-08-08
DE69620445D1 (de)	2002-05-08
EE03484B1 (et)	2001-08-15
DK0865440T3 (da)	2002-07-22
HK1042482A1 (en)	2002-08-16
DE69620445T2 (de)	2002-12-12
HUP9900185A3 (en)	1999-11-29
CZ157398A3 (cs)	1998-10-14
UA57717C2 (uk)	2003-07-15
JPH10511405A (ja)	1998-11-04
BG102458A (en)	1999-06-30
JP3257559B2 (ja)	2002-02-18
HRP960576A2 (en)	1998-02-28
SK70498A3 (en)	1998-10-07
ES2175137T3 (es)	2002-11-16
BR9610745A (pt)	1999-07-13
CA2231105C (en)	2005-09-13
KR19990063891A (ko)	1999-07-26
SI1162201T1 (sl)	2006-08-31
SK283335B6 (sk)	2003-06-03
AR004992A1 (es)	1999-04-07
ES2260156T3 (es)	2006-11-01
NO980927L (no)	1998-06-08
ZA9610254B (en)	1998-06-05
PT1162201E (pt)	2006-08-31

Legal Events

Date	Code	Title	Description
2016-10-24	MK1K	Patent expired

Publication	Publication Date	Title
NO314036B1 (no)	2003-01-20	Farnesylproteintransferase-inhiberende (imidazol-5-yl)metyl-2- kinolinonderivater
EP1019395B1 (de)	2002-01-30	Farnesyltransferase hemmende 2-chinolonderivate
US6187786B1 (en)	2001-02-13	Farnesyl transferase inhibiting 1,8-annelated quinolinone derivatives substituted with N- or C-linked imidazoles
IL130363A (en)	2002-08-14	Quinazolines that inhibit frenzyl transferase, their preparation and pharmaceutical preparations containing them
US7067531B2 (en)	2006-06-27	Farnesyl transferase inhibiting 6-heterocyclylmethyl quinolinone derivatives
HK1012188B (en)	2002-07-26	Farnesyl protein transferase inhibiting (imidazol-5-yl) methyl-2-quinolinone derivatives
HK1027576B (en)	2002-05-24	Farnesyl transferase inhibiting 2-quinolone derivatives
HK1036064B (en)	2004-11-19	Farnesyl transferase inhibiting 2-quinolone derivatives
MXPA98002067A (en)	1998-11-12	Derivatives of the 2-quinolone inhibitors of the farnesil transfer