ZA200103419B - Certain substituted caprolactams, pharmaceutical compositions containing them and their use in treating tumors. - Google Patents
Certain substituted caprolactams, pharmaceutical compositions containing them and their use in treating tumors. Download PDFInfo
- Publication number
- ZA200103419B ZA200103419B ZA200103419A ZA200103419A ZA200103419B ZA 200103419 B ZA200103419 B ZA 200103419B ZA 200103419 A ZA200103419 A ZA 200103419A ZA 200103419 A ZA200103419 A ZA 200103419A ZA 200103419 B ZA200103419 B ZA 200103419B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- hydrogen
- pharmaceutically acceptable
- alkyl
- Prior art date
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- 206010028980 Neoplasm Diseases 0.000 title claims description 29
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- -1 4-n-decylphenyl Chemical group 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 28
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
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- 125000004419 alkynylene group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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- 239000001301 oxygen Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 6
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 230000003676 hair loss Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 230000002962 histologic effect Effects 0.000 description 1
- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 239000004310 lactic acid Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000021266 loss of appetite Nutrition 0.000 description 1
- 208000019017 loss of appetite Diseases 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 201000000050 myeloid neoplasm Diseases 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011580 nude mouse model Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000001384 succinic acid Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011975 tartaric acid Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical group CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19335498A | 1998-11-17 | 1998-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200103419B true ZA200103419B (en) | 2002-06-26 |
Family
ID=22713307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200103419A ZA200103419B (en) | 1998-11-17 | 2001-04-26 | Certain substituted caprolactams, pharmaceutical compositions containing them and their use in treating tumors. |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1131297B1 (de) |
| JP (1) | JP3550545B2 (de) |
| KR (1) | KR20010080461A (de) |
| CN (1) | CN1187333C (de) |
| AR (1) | AR023914A1 (de) |
| AT (1) | ATE264309T1 (de) |
| AU (1) | AU748016B2 (de) |
| BR (1) | BR9915436A (de) |
| CA (1) | CA2347773C (de) |
| CO (1) | CO5140099A1 (de) |
| CZ (1) | CZ20011707A3 (de) |
| DE (1) | DE69916488T2 (de) |
| ES (1) | ES2221463T3 (de) |
| HU (1) | HUP0104224A3 (de) |
| ID (1) | ID28343A (de) |
| IL (1) | IL142701A0 (de) |
| NO (1) | NO20012428L (de) |
| PE (1) | PE20001241A1 (de) |
| PL (1) | PL347633A1 (de) |
| PT (1) | PT1131297E (de) |
| SK (1) | SK6692001A3 (de) |
| TR (1) | TR200101366T2 (de) |
| UY (2) | UY25807A1 (de) |
| WO (1) | WO2000029382A1 (de) |
| ZA (1) | ZA200103419B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1282604B1 (de) * | 2000-05-11 | 2008-01-09 | Novartis AG | Substituierte caprolactam carbonate und ether sowie deren verwendung als anti-tumor wirkstoffe |
| US6545148B2 (en) | 2001-03-12 | 2003-04-08 | Novartis Ag | Process for preparing certain substituted caprolactams |
| MXPA06000975A (es) | 2003-07-25 | 2006-04-11 | Novartis Ag | Lactams sustituidos y su uso como agentes anti-cancer. |
| US7153846B2 (en) | 2003-10-24 | 2006-12-26 | Sanofi-Aventis Deutschland Gmbh | Bengamide derivatives, process for preparing them, and their use |
| DE10349669B3 (de) * | 2003-10-24 | 2005-05-25 | Aventis Pharma Deutschland Gmbh | Bengamide-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| FR2878525B1 (fr) * | 2004-11-29 | 2007-02-23 | Aventis Pharma Sa | Bengamides possedant un cycle caprolactame substitue, procede de preparation, compositions les contenant et utilisation |
| FR2878528B1 (fr) * | 2004-11-29 | 2008-05-16 | Aventis Pharma Sa | 2-alcoxy-3,4,5-trihydroxy-alkylamides, leur preparation, compositions les contenant et utilisation |
| FR2901554B1 (fr) | 2006-05-24 | 2011-04-01 | Sanofi Aventis | 2-alcoxy-3,4,5-trihydroxy-alkylamide-benzazepine, leur preparation, compositions les contenant et utilisation |
| FR2901556A1 (fr) | 2006-05-24 | 2007-11-30 | Sanofi Aventis Sa | Derives de 2-alcoxy-3,4,5-trihydroxy-alkylamide, leur preparation, compositions les contenant et utilisation |
| FR2901555A1 (fr) | 2006-05-24 | 2007-11-30 | Sanofi Aventis Sa | 2-alcoxy-3,4,5-trihydroxy-alkylamide-benzothiazepine, leur preparation, compositions les contenant et utilisation |
| WO2011157793A1 (en) | 2010-06-17 | 2011-12-22 | Novartis Ag | Piperidinyl substituted 1,3-dihydro-benzoimidazol-2-ylideneamine derivatives |
| WO2011157787A1 (en) | 2010-06-17 | 2011-12-22 | Novartis Ag | Biphenyl substituted 1,3-dihydro-benzoimidazol-2-ylideneamine derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9411841D0 (en) * | 1994-06-14 | 1994-08-03 | Pharma Mar Sa | New antitumoral compounds from jaspis sponge |
-
1999
- 1999-11-04 CO CO99069674A patent/CO5140099A1/es unknown
- 1999-11-15 JP JP2000582369A patent/JP3550545B2/ja not_active Expired - Fee Related
- 1999-11-15 IL IL14270199A patent/IL142701A0/xx unknown
- 1999-11-15 TR TR2001/01366T patent/TR200101366T2/xx unknown
- 1999-11-15 CA CA002347773A patent/CA2347773C/en not_active Expired - Fee Related
- 1999-11-15 KR KR1020017006152A patent/KR20010080461A/ko not_active Application Discontinuation
- 1999-11-15 ES ES99957309T patent/ES2221463T3/es not_active Expired - Lifetime
- 1999-11-15 DE DE69916488T patent/DE69916488T2/de not_active Expired - Lifetime
- 1999-11-15 PL PL99347633A patent/PL347633A1/xx unknown
- 1999-11-15 PE PE1999001155A patent/PE20001241A1/es not_active Application Discontinuation
- 1999-11-15 CN CNB998134104A patent/CN1187333C/zh not_active Expired - Fee Related
- 1999-11-15 BR BR9915436-6A patent/BR9915436A/pt not_active Application Discontinuation
- 1999-11-15 HU HU0104224A patent/HUP0104224A3/hu unknown
- 1999-11-15 AU AU15060/00A patent/AU748016B2/en not_active Ceased
- 1999-11-15 PT PT99957309T patent/PT1131297E/pt unknown
- 1999-11-15 WO PCT/EP1999/008767 patent/WO2000029382A1/en active IP Right Grant
- 1999-11-15 EP EP99957309A patent/EP1131297B1/de not_active Expired - Lifetime
- 1999-11-15 AR ARP990105796A patent/AR023914A1/es unknown
- 1999-11-15 CZ CZ20011707A patent/CZ20011707A3/cs unknown
- 1999-11-15 AT AT99957309T patent/ATE264309T1/de not_active IP Right Cessation
- 1999-11-15 SK SK669-2001A patent/SK6692001A3/sk unknown
- 1999-11-15 ID IDW00200100966A patent/ID28343A/id unknown
- 1999-11-17 UY UY25807A patent/UY25807A1/es unknown
-
2000
- 2000-02-25 UY UY26036A patent/UY26036A1/es unknown
-
2001
- 2001-04-26 ZA ZA200103419A patent/ZA200103419B/en unknown
- 2001-05-16 NO NO20012428A patent/NO20012428L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL347633A1 (en) | 2002-04-22 |
| DE69916488D1 (de) | 2004-05-19 |
| TR200101366T2 (tr) | 2001-10-22 |
| CN1187333C (zh) | 2005-02-02 |
| UY25807A1 (es) | 2001-08-27 |
| ATE264309T1 (de) | 2004-04-15 |
| BR9915436A (pt) | 2001-08-07 |
| NO20012428D0 (no) | 2001-05-16 |
| JP3550545B2 (ja) | 2004-08-04 |
| JP2002529536A (ja) | 2002-09-10 |
| SK6692001A3 (en) | 2001-10-08 |
| EP1131297B1 (de) | 2004-04-14 |
| HUP0104224A3 (en) | 2002-04-29 |
| ES2221463T3 (es) | 2004-12-16 |
| CA2347773C (en) | 2009-03-10 |
| AR023914A1 (es) | 2002-09-04 |
| CN1326445A (zh) | 2001-12-12 |
| IL142701A0 (en) | 2002-03-10 |
| CO5140099A1 (es) | 2002-03-22 |
| PE20001241A1 (es) | 2000-11-24 |
| UY26036A1 (es) | 2001-06-29 |
| DE69916488T2 (de) | 2005-03-24 |
| WO2000029382A1 (en) | 2000-05-25 |
| HUP0104224A2 (hu) | 2002-03-28 |
| CA2347773A1 (en) | 2000-05-25 |
| ID28343A (id) | 2001-05-17 |
| CZ20011707A3 (cs) | 2001-08-15 |
| NO20012428L (no) | 2001-07-17 |
| KR20010080461A (ko) | 2001-08-22 |
| EP1131297A1 (de) | 2001-09-12 |
| AU748016B2 (en) | 2002-05-30 |
| AU1506000A (en) | 2000-06-05 |
| PT1131297E (pt) | 2004-08-31 |
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