NO318922B1 - 1,2-annelerte kinolinderivater - Google Patents
1,2-annelerte kinolinderivater Download PDFInfo
- Publication number
- NO318922B1 NO318922B1 NO20013088A NO20013088A NO318922B1 NO 318922 B1 NO318922 B1 NO 318922B1 NO 20013088 A NO20013088 A NO 20013088A NO 20013088 A NO20013088 A NO 20013088A NO 318922 B1 NO318922 B1 NO 318922B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- hydrogen
- compounds
- chlorophenyl
- radical
- Prior art date
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- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 149
- 239000000543 intermediate Substances 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 239000001257 hydrogen Substances 0.000 claims description 84
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 37
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- -1 aminocarbonylcarbonyl Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 230000009466 transformation Effects 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- HGDNILFTURGNIL-UHFFFAOYSA-N (4-chlorophenyl)-[5-(3-chlorophenyl)tetrazolo[1,5-a]quinolin-7-yl]-(3-methylimidazol-4-yl)methanamine Chemical compound CN1C=NC=C1C(N)(C=1C=C2C(N3N=NN=C3C=C2C=2C=C(Cl)C=CC=2)=CC=1)C1=CC=C(Cl)C=C1 HGDNILFTURGNIL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
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- RDBBFCMDRBOXIG-UHFFFAOYSA-N quinolin-7-ylmethanol Chemical compound C1=CC=NC2=CC(CO)=CC=C21 RDBBFCMDRBOXIG-UHFFFAOYSA-N 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- SUMXFQRFMMRQJN-UHFFFAOYSA-N (4-chlorophenyl)-(3-methylimidazol-4-yl)-(5-phenylimidazo[1,2-a]quinolin-7-yl)methanol Chemical compound CN1C=NC=C1C(O)(C=1C=C2C(N3C=CN=C3C=C2C=2C=CC=CC=2)=CC=1)C1=CC=C(Cl)C=C1 SUMXFQRFMMRQJN-UHFFFAOYSA-N 0.000 claims description 2
- HQMMMMYFNVTBTJ-UHFFFAOYSA-N (4-chlorophenyl)-[5-(3-chlorophenyl)imidazo[1,2-a]quinolin-7-yl]-(3-methylimidazol-4-yl)methanol Chemical compound CN1C=NC=C1C(O)(C=1C=C2C(N3C=CN=C3C=C2C=2C=C(Cl)C=CC=2)=CC=1)C1=CC=C(Cl)C=C1 HQMMMMYFNVTBTJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910010084 LiAlH4 Inorganic materials 0.000 claims description 2
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- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004997 halocarbonyl group Chemical group 0.000 claims description 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- VLYOWFSEQNDOCR-UHFFFAOYSA-N (4-chlorophenyl)-(3-methylimidazol-4-yl)-[5-(3-methylphenyl)tetrazolo[1,5-a]quinolin-7-yl]methanamine Chemical compound CC1=CC=CC(C=2C3=CC(=CC=C3N3N=NN=C3C=2)C(N)(C=2N(C=NC=2)C)C=2C=CC(Cl)=CC=2)=C1 VLYOWFSEQNDOCR-UHFFFAOYSA-N 0.000 claims 1
- JUMDFLZNHJCMKW-UHFFFAOYSA-N (4-chlorophenyl)-[5-(3-chlorophenyl)-1,5-dihydrotetrazolo[1,5-a]quinazolin-7-yl]-(3-methylimidazol-4-yl)methanol Chemical compound CN1C=NC=C1C(O)(C=1C=C2C(N3N=NN=C3NC2C=2C=C(Cl)C=CC=2)=CC=1)C1=CC=C(Cl)C=C1 JUMDFLZNHJCMKW-UHFFFAOYSA-N 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
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- 239000003480 eluent Substances 0.000 description 18
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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Classifications
-
- 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
-
- 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
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- 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
- A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D471/04—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)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Information Retrieval, Db Structures And Fs Structures Therefor (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98204444 | 1998-12-23 | ||
PCT/EP1999/010214 WO2000039082A2 (en) | 1998-12-23 | 1999-12-17 | 1,2-annelated quinoline derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20013088D0 NO20013088D0 (no) | 2001-06-21 |
NO20013088L NO20013088L (no) | 2001-06-21 |
NO318922B1 true NO318922B1 (no) | 2005-05-23 |
Family
ID=8234557
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20013088A NO318922B1 (no) | 1998-12-23 | 2001-06-21 | 1,2-annelerte kinolinderivater |
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US (2) | US6458800B1 (id) |
EP (1) | EP1140935B1 (id) |
JP (1) | JP4725940B2 (id) |
KR (2) | KR100712226B1 (id) |
CN (1) | CN1178938C (id) |
AR (1) | AR021995A1 (id) |
AT (1) | ATE240327T1 (id) |
AU (1) | AU765437B2 (id) |
BG (1) | BG65124B1 (id) |
BR (1) | BR9916827A (id) |
CA (1) | CA2355717C (id) |
CZ (1) | CZ302374B6 (id) |
DE (1) | DE69907964T2 (id) |
DK (1) | DK1140935T3 (id) |
EA (1) | EA004542B1 (id) |
EE (1) | EE04962B1 (id) |
ES (1) | ES2200591T3 (id) |
HK (1) | HK1038746B (id) |
HR (1) | HRP20010454B1 (id) |
HU (1) | HU229404B1 (id) |
ID (1) | ID29241A (id) |
IL (2) | IL143859A0 (id) |
NO (1) | NO318922B1 (id) |
PL (1) | PL199080B1 (id) |
PT (1) | PT1140935E (id) |
SI (1) | SI1140935T1 (id) |
SK (1) | SK286072B6 (id) |
TR (1) | TR200101961T2 (id) |
TW (1) | TW531533B (id) |
UA (1) | UA71592C2 (id) |
WO (1) | WO2000039082A2 (id) |
ZA (1) | ZA200105136B (id) |
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SI1255537T1 (sl) * | 2000-02-04 | 2006-10-31 | Janssen Pharmaceutica Nv | Inhibitorji farnezil protein transferaze za zdravljenje raka dojk |
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AU2001242434A1 (en) * | 2000-02-29 | 2001-09-12 | Janssen Pharmaceutica N.V. | Farnesyl protein transferase inhibitor combinations with vinca alkaloids |
AU2001254672A1 (en) * | 2000-02-29 | 2001-09-12 | Janssen Pharmaceutica N.V. | Farnesyl protein transferase inhibitor combinations with an her2 antibody |
JP2003525235A (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 | 抗腫瘍ヌクレオシド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の組み合わせ剤 |
JP2003525246A (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 | 白金化合物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の組み合わせ剤 |
CA2397446A1 (en) * | 2000-02-29 | 2001-09-07 | Janssen Pharmaceutica Inc. | Combinations of a farnesyl protein transferase inhibitor with nitrogen mustard or nitrosourea alkylating agents |
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DE60118225T2 (de) * | 2000-09-25 | 2007-05-03 | Janssen Pharmaceutica N.V. | Chinolin- und chinazolinderivate und deren verwendung als farnesyl transferase inhibitoren |
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JP4351445B2 (ja) | 2000-12-27 | 2009-10-28 | 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4−置換−キノリンおよびキナゾリン誘導体 |
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JP2005519876A (ja) * | 2001-11-27 | 2005-07-07 | メルク エンド カムパニー インコーポレーテッド | 2−アミノキノリン化合物 |
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CA2002864C (en) | 1988-11-29 | 1999-11-16 | Eddy J. E. Freyne | (1h-azol-1-ylmethyl) substituted quinoline, quinazoline or quinoxaline derivatives |
TW349948B (en) * | 1995-10-31 | 1999-01-11 | Janssen Pharmaceutica Nv | Farnesyl transferase inhibiting 2-quinolone derivatives |
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RU2205831C2 (ru) * | 1997-04-25 | 2003-06-10 | Янссен Фармацевтика Н.В. | Хиназолиноны, ингибирующие фарнезилтрансферазу |
IL133212A (en) * | 1997-06-02 | 2005-12-18 | Janssen Pharmaceutica Nv | History of use (imidazolil-5-yl) methyl-2-quinolinone that act as culture inhibitors of smooth muscle cells |
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