SK33099A3 - Novel tricyclic piperidinyl compounds useful as inhibitors of farnesyl-protein transferase - Google Patents
Novel tricyclic piperidinyl compounds useful as inhibitors of farnesyl-protein transferase Download PDFInfo
- Publication number
- SK33099A3 SK33099A3 SK330-99A SK33099A SK33099A3 SK 33099 A3 SK33099 A3 SK 33099A3 SK 33099 A SK33099 A SK 33099A SK 33099 A3 SK33099 A3 SK 33099A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- benzo
- dihydro
- cyclohepta
- dichloromethane
- Prior art date
Links
- 125000003386 piperidinyl group Chemical group 0.000 title claims description 12
- 102000004357 Transferases Human genes 0.000 title abstract description 16
- 108090000992 Transferases Proteins 0.000 title abstract description 16
- 239000003112 inhibitor Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 178
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 57
- 125000003118 aryl group Chemical group 0.000 claims abstract description 49
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 16
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 14
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 13
- 230000002159 abnormal effect Effects 0.000 claims abstract description 12
- 230000010261 cell growth Effects 0.000 claims abstract description 12
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 239000012453 solvate Substances 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 395
- -1 benzotriazol-yloxyl Chemical group 0.000 claims description 108
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 102000016914 ras Proteins Human genes 0.000 claims description 24
- 108010014186 ras Proteins Proteins 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 210000004881 tumor cell Anatomy 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 210000004027 cell Anatomy 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 150000003857 carboxamides Chemical class 0.000 claims description 9
- 108090000623 proteins and genes Proteins 0.000 claims description 9
- 108700042226 ras Genes Proteins 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 230000035772 mutation Effects 0.000 claims description 7
- 231100000590 oncogenic Toxicity 0.000 claims description 7
- 230000002246 oncogenic effect Effects 0.000 claims description 7
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 201000002528 pancreatic cancer Diseases 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 208000029742 colonic neoplasm Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000003949 imides Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 206010005003 Bladder cancer Diseases 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 101150040459 RAS gene Proteins 0.000 claims description 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 3
- 230000003325 follicular Effects 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 3
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- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 208000025113 myeloid leukemia Diseases 0.000 claims description 3
- 210000001685 thyroid gland Anatomy 0.000 claims description 3
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
- 150000008575 L-amino acids Chemical class 0.000 claims description 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
- 210000000066 myeloid cell Anatomy 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 1
- 125000003147 glycosyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 61
- 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 abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 12
- 241000124008 Mammalia Species 0.000 abstract description 5
- 102000004190 Enzymes Human genes 0.000 abstract description 2
- 108090000790 Enzymes Proteins 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 84
- 239000011541 reaction mixture Substances 0.000 description 77
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 72
- 239000000243 solution Substances 0.000 description 69
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 66
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
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- 239000000047 product Substances 0.000 description 47
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- 239000000908 ammonium hydroxide Substances 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 37
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 36
- 235000019341 magnesium sulphate Nutrition 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 239000000203 mixture Substances 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
- 239000010410 layer Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 23
- 230000005764 inhibitory process Effects 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 19
- 239000002253 acid Substances 0.000 description 17
- 125000003545 alkoxy group Chemical group 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 150000003973 alkyl amines Chemical class 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229910052786 argon Inorganic materials 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 13
- 125000005265 dialkylamine group Chemical group 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
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- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
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- KWAARCUDDHAJGQ-UHFFFAOYSA-N 1-(3-bromo-8-chloro-6,11-dihydro-5h-benzo[1,2]cyclohepta[2,4-b]pyridin-11-yl)piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1C2=NC=C(Br)C=C2CCC2=CC(Cl)=CC=C21 KWAARCUDDHAJGQ-UHFFFAOYSA-N 0.000 description 9
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
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- BCXDLZPZAGHJHB-UHFFFAOYSA-N 3,10-dibromo-8,10-dichloro-5,6,9,11-tetrahydrobenzo[7,8]cyclohepta[1,2-b]pyridine Chemical compound C1C2=NC=C(Br)C=C2CCC2=C1C(Cl)(Br)CC(Cl)=C2 BCXDLZPZAGHJHB-UHFFFAOYSA-N 0.000 description 6
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
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- ZRJIVKUVYZIQNN-UHFFFAOYSA-N tert-butyl 4-(pyridin-4-ylcarbamoyl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(=O)NC1=CC=NC=C1 ZRJIVKUVYZIQNN-UHFFFAOYSA-N 0.000 description 1
- KOTJMIJSYFYROE-UHFFFAOYSA-N tert-butyl 4-[3-oxo-3-(pyridin-3-ylmethylamino)propyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCC(=O)NCC1=CC=CN=C1 KOTJMIJSYFYROE-UHFFFAOYSA-N 0.000 description 1
- DYDSKSOVXWWYQZ-UHFFFAOYSA-N tert-butyl cyanate Chemical compound CC(C)(C)OC#N DYDSKSOVXWWYQZ-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
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
- C07D401/14—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
-
- 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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71370396A | 1996-09-13 | 1996-09-13 | |
| PCT/US1997/015903 WO1998011098A1 (en) | 1996-09-13 | 1997-09-11 | Novel tricyclic piperidinyl compounds useful as inhibitors of farnesyl-protein transferase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK33099A3 true SK33099A3 (en) | 2000-05-16 |
Family
ID=24867181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK330-99A SK33099A3 (en) | 1996-09-13 | 1997-09-11 | Novel tricyclic piperidinyl compounds useful as inhibitors of farnesyl-protein transferase |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0931078B1 (es) |
| JP (1) | JP2001500507A (es) |
| KR (1) | KR20000036104A (es) |
| CN (1) | CN1237170A (es) |
| AT (1) | ATE345338T1 (es) |
| AU (1) | AU4337697A (es) |
| BR (1) | BR9712826A (es) |
| CA (1) | CA2265763A1 (es) |
| CZ (1) | CZ84199A3 (es) |
| DE (1) | DE69736950T2 (es) |
| ES (1) | ES2276435T3 (es) |
| HU (1) | HUP0000191A2 (es) |
| ID (1) | ID21218A (es) |
| NO (1) | NO991233L (es) |
| NZ (1) | NZ334452A (es) |
| PL (1) | PL332241A1 (es) |
| SK (1) | SK33099A3 (es) |
| TR (1) | TR199901274T2 (es) |
| WO (1) | WO1998011098A1 (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6433165B1 (en) | 1998-01-21 | 2002-08-13 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| CA2319077A1 (en) | 1998-01-21 | 1999-07-29 | Yoshisuke Nakasato | Chemokine receptor antagonists and methods of use therefor |
| US6509346B2 (en) | 1998-01-21 | 2003-01-21 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US6613905B1 (en) | 1998-01-21 | 2003-09-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US6503926B2 (en) | 1998-09-04 | 2003-01-07 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US6288083B1 (en) | 1998-09-04 | 2001-09-11 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US7271176B2 (en) | 1998-09-04 | 2007-09-18 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use thereof |
| US6645966B2 (en) | 2001-01-22 | 2003-11-11 | Schering Corporation | Treatment of malaria with farnesyl protein transferase inhibitors |
| AU2002257114A1 (en) * | 2001-04-06 | 2002-10-21 | Schering Corporation | Treatment of malaria with farsenyl protein transferase inhibitors |
| US7541365B2 (en) | 2001-11-21 | 2009-06-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| TWI291467B (en) | 2002-11-13 | 2007-12-21 | Millennium Pharm Inc | CCR1 antagonists and methods of use therefor |
| NZ551603A (en) * | 2004-06-24 | 2010-11-26 | Incyte Corp | N-substituted piperidines and their use as pharmaceuticals |
| WO2008045673A2 (en) * | 2006-10-06 | 2008-04-17 | Bausch & Lomb Incorporated | Quinolone carboxylic acids, derivatives thereof, processes for its preparation and its use as antibacterial agents |
| US7632944B2 (en) * | 2007-01-24 | 2009-12-15 | Bausch & Lomb Incorporated | Quinolone carboxylic acids, derivatives thereof, and methods of making and using same |
| US20110136790A1 (en) * | 2008-07-23 | 2011-06-09 | De Lera Ruiz Manuel | Tricyclic Heterocyclic Derivatives and Methods of Use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1593417A (en) * | 1976-12-22 | 1981-07-15 | Squibb & Sons Inc | Carbocyclic-fused pyrazolopyridine derivatives |
| US5089496A (en) * | 1986-10-31 | 1992-02-18 | Schering Corporation | Benzo[5,6]cycloheptapyridine compounds, compositions and method of treating allergies |
| IL98572A (en) * | 1990-06-22 | 1995-07-31 | Schering Corp | Bite-benzo or benzopyrido compounds Cyclohepta piperidine, piperidylidene and piperazine, preparations and methods of use. |
| JP2875393B2 (ja) * | 1993-10-15 | 1999-03-31 | シェーリング コーポレイション | Ｇ−タンパク質機能の阻害および増殖性疾患の治療に有用な三環式カルバメート化合物 |
| IL111235A (en) * | 1993-10-15 | 2001-03-19 | Schering Plough Corp | Medicinal preparations for inhibiting protein G activity and for the treatment of malignant diseases, containing tricyclic compounds, some such new compounds and a process for the preparation of some of them |
-
1997
- 1997-09-11 CN CN97199599A patent/CN1237170A/zh active Pending
- 1997-09-11 DE DE69736950T patent/DE69736950T2/de not_active Expired - Fee Related
- 1997-09-11 ID IDW990091A patent/ID21218A/id unknown
- 1997-09-11 AU AU43376/97A patent/AU4337697A/en not_active Abandoned
- 1997-09-11 EP EP97941477A patent/EP0931078B1/en not_active Expired - Lifetime
- 1997-09-11 PL PL97332241A patent/PL332241A1/xx unknown
- 1997-09-11 ES ES97941477T patent/ES2276435T3/es not_active Expired - Lifetime
- 1997-09-11 WO PCT/US1997/015903 patent/WO1998011098A1/en active IP Right Grant
- 1997-09-11 CA CA002265763A patent/CA2265763A1/en not_active Abandoned
- 1997-09-11 CZ CZ99841A patent/CZ84199A3/cs unknown
- 1997-09-11 SK SK330-99A patent/SK33099A3/sk unknown
- 1997-09-11 KR KR1019997002127A patent/KR20000036104A/ko not_active Application Discontinuation
- 1997-09-11 AT AT97941477T patent/ATE345338T1/de not_active IP Right Cessation
- 1997-09-11 JP JP10513762A patent/JP2001500507A/ja not_active Ceased
- 1997-09-11 BR BR9712826-0A patent/BR9712826A/pt unknown
- 1997-09-11 TR TR1999/01274T patent/TR199901274T2/xx unknown
- 1997-09-11 NZ NZ334452A patent/NZ334452A/xx unknown
- 1997-09-11 HU HU0000191A patent/HUP0000191A2/hu unknown
-
1999
- 1999-03-12 NO NO991233A patent/NO991233L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1237170A (zh) | 1999-12-01 |
| DE69736950T2 (de) | 2007-09-20 |
| TR199901274T2 (xx) | 1999-10-21 |
| BR9712826A (pt) | 1999-11-16 |
| ATE345338T1 (de) | 2006-12-15 |
| EP0931078B1 (en) | 2006-11-15 |
| PL332241A1 (en) | 1999-08-30 |
| CZ84199A3 (cs) | 1999-11-17 |
| EP0931078A1 (en) | 1999-07-28 |
| KR20000036104A (ko) | 2000-06-26 |
| HUP0000191A2 (hu) | 2001-04-28 |
| AU4337697A (en) | 1998-04-02 |
| CA2265763A1 (en) | 1998-03-19 |
| WO1998011098A1 (en) | 1998-03-19 |
| NZ334452A (en) | 2000-09-29 |
| ES2276435T3 (es) | 2007-06-16 |
| DE69736950D1 (de) | 2006-12-28 |
| JP2001500507A (ja) | 2001-01-16 |
| NO991233D0 (no) | 1999-03-12 |
| NO991233L (no) | 1999-05-12 |
| ID21218A (id) | 1999-05-06 |
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