Claims for Patent: 7,834,019
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Summary for Patent: 7,834,019
Title: | Substituted pyrazolo[3,4-d]pyrimidinone derivatives |
Abstract: | The invention relates to compounds of a general formula (I): ##STR00001## wherein Ar.sup.1 is an optionally-substituted aryl or heteroaromatic group; R.sup.1 is an optionally-substituted lower alkyl, lower alkenyl, lower alkynyl or cyclo-lower alkyl group, or is an aryl, aralkyl or heteroaromatic group optionally having a substituent; R.sup.2 is a hydrogen atom, a lower alkyl group, a lower alkenyl group or a lower alkynyl group, or is an aryl, aralkyl or heteroaromatic group optionally having a substituent; R.sup.3 is a hydrogen atom or a lower alkyl group; R.sup.4 is a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group or a group of --N(R.sup.1k)R.sup.1m; T and U are a nitrogen atom or a methine group, etc. The compounds of the invention have excellent Weel kinase-inhibitory effect and are therefore useful in the field of medicines, especially treatment of various cancers. |
Inventor(s): | Sagara; Takeshi (Tsukuba, JP), Otsuki; Sachie (Tsukuba, JP), Sunami; Satoshi (Toride, JP), Sakamoto; Toshihiro (Moriya, JP), Niiyama; Kenji (Tsuchiura, JP), Yamamoto; Fuyuki (Tsukuba, JP), Yoshizumi; Takashi (Ushiku, JP), Furuyama; Hidetomo (Tsukuba, JP), Goto; Yasuhiro (Tsukuba, JP), Bamba; Makoto (Tsukuba, JP), Takahashi; Keiji (Tsukuba, JP), Hirai; Hiroshi (Tsukuba, JP), Nishibata; Toshihide (Tsukuba, JP) |
Assignee: | Banyu Pharmaceutical Co., Ltd. (Chiyoda-Ku, Tokyo, JP) |
Application Number: | 11/789,548 |
Patent Claims: | 1. A compound of formula (I): ##STR00216## wherein; Ar.sup.1 is an aryl group or a heteroaromatic group, which is optionally substituted with a substituent selected
from the group consisting of a halogen atom, a lower alkyl group, a halo-lower alkyl group, a hydroxy-lower alkyl group, a lower alkoxy group, a lower alkanoyl group, a hydroxy-lower alkylamino group, a carbamoyl group, a hydroxy-lower alkylcarbamoyl
group, a heteroaromatic group optionally substituted by a lower alkyl group, and a group of -Q.sup.1-A.sup.1-Q.sup.2-A.sup.2(R.sup.1a)R.sup.1b; A.sup.1 is a single bond, an oxygen atom or a sulfur atom, or is an imino group optionally substituted by a
lower alkyl group; A.sup.2 is a nitrogen atom, or is a methine or 1-vinyl-2-ylidene group optionally substituted by a hydroxyl group, a lower alkyl group or a hydroxy-lower alkyl group; Q.sup.1 is a single bond, a carbonyl group, or a methylene group
optionally substituted by a lower alkyl group; Q.sup.2 is a single bond, or an ethylene group optionally substituted by a lower alkyl group; R.sup.1a is a hydrogen atom, a lower alkyl group or a hydroxy-lower alkyl group, R.sup.1b is a hydrogen atom, a
lower alkyl group or a hydroxy-lower alkyl group, or R.sup.1a and R.sup.1b together form a lower alkylene group wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a sulfur
atom, a sulfinyl group, a sulfonyl group, a carbonyl group, a vinylene group or a group of --N(R.sup.1c)--, or substituted by a hydroxyl group or a lower alkyl group; R.sup.1c is a hydrogen atom, a lower alkenyl group or a group of
-Q.sup.3-A.sup.3(R.sup.1d)R.sup.1e; A.sup.3 is a nitrogen atom, or is a methine or 1-vinyl-2-ylidene group optionally substituted by a hydroxyl group, a lower alkyl group or a hydroxy-lower alkyl group; Q.sup.3 is a single bond or a lower alkylene
group, wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a sulfur atom, a carbonyl group, a sulfinyl group or a sulfonyl group, and/or substituted by a halogen atom, a cyano
group, a hydroxyl group or a lower alkyl group; R.sup.1d is a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a lower alkyl group or a hydroxy-lower alkyl group, R.sup.1e is a hydrogen atom, a halogen atom, a cyano group, a hydroxyl
group, a lower alkyl group or a hydroxy-lower alkyl group, or R.sup.1d and R.sup.1e together form a lower alkylene group wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a
sulfur atom, a sulfinyl group, a sulfonyl group, a carbonyl group, a vinylene group or a group of --N(R.sup.1f)--, and/or substituted by a hydroxyl group or a lower alkyl group; R.sup.1f is a hydrogen atom, a lower alkyl group, a halo-lower alkyl group,
a lower alkenyl group or a lower alkanoyl group; R.sup.1 is a lower alkenyl group, optionally substituted by a halogen atom; R.sup.2 is a hydrogen atom, a lower alkyl group, a lower alkenyl group or a lower alkynyl group, or is an aryl group, an
aralkyl group or a heteroaromatic group optionally having a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a carboxyl group, a group of -Q.sup.4-A.sup.4(R.sup.1g)R.sup.1h and a group of -Q.sup.5-Ar.sup.a,
wherein one or two or more methylene groups constituting the lower alkyl group, the lower alkenyl group or the lower alkynyl group may be independently replaced by an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, a carbonyl group or a
group of --N(R.sup.1j)--, or substituted by a halogen atom; A.sup.4 is a nitrogen atom, or is a methine group optionally substituted by a halogen atom, a hydroxyl group, a lower alkyl group or a hydroxy-lower alkyl group; Ar.sup.a is an aryl group or a
heteroaromatic group, which may have a substituent selected from a group consisting of a halogen atom, a lower alkyl group, a halo-lower alkyl group, a hydroxy-lower alkyl group and a lower alkoxy group; Q.sup.4 is a single bond or a lower alkylene
group, wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom or a carbonyl group, or substituted by a lower alkyl group; Q.sup.5 is a single bond, an oxygen atom, a sulfur atom,
a carbonyl group or a lower alkylene group, wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a sulfur atom or a carbonyl group, or substituted by a halogen atom or a lower
alkyl group; R.sup.1g is a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a lower alkyl group, a lower alkoxy-lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group or a lower alkylsulfonyl group, R.sup.1h is a hydrogen
atom, a halogen atom, a cyano group, a hydroxyl group, a lower alkyl group, a lower alkoxy-lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group or a lower alkylsulfonyl group, or R.sup.1g and R.sup.1h together form a lower alkylene
group, wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, a carbonyl group or a group of --N(R.sup.1i)--, and/or
substituted by a halogen atom or a lower alkyl group; R.sup.1i is a hydrogen atom, a lower alkyl group or a halo-lower alkyl group; R.sup.1j is a hydrogen atom or a lower alkyl group; R.sup.3 is a hydrogen atom or a lower alkyl group; R.sup.4 is a
hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group or a group of --N(R.sup.1k)R.sup.1m; R.sup.1k is a hydrogen atom or a lower alkyl group; R.sup.1m is a hydrogen atom or a lower alkyl group; T is a nitrogen atom; U is a nitrogen
atom or a salt thereof.
2. The compound of formula (I-1) as claimed in claim 1, or a salt thereof: ##STR00217## wherein, A.sup.1 is a single bond, an oxygen atom or a sulfur atom, or is an imino group optionally substituted by a lower alkyl group; A.sup.2 is a nitrogen atom, or is a methine or 1-vinyl-2-ylidene group optionally substituted by a hydroxyl group, a lower alkyl group or a hydroxy-lower alkyl group; Q.sup.1 is a single bond, a carbonyl group, or a methylene group optionally substituted by a lower alkyl group; Q.sup.2 is a single bond, or an ethylene group optionally substituted by a lower alkyl group; R.sup.1a is a hydrogen atom, a lower alkyl group or a hydroxy-lower alkyl group, R.sup.1b is a hydrogen atom, a lower alkyl group or a hydroxy-lower alkyl group, or R.sup.1a and R.sup.1b together form a lower alkylene group wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, a carbonyl group, a vinylene group or a group of --N(R.sup.1c)--, and/or substituted by a hydroxyl group or a lower alkyl group; R.sup.1c is a hydrogen atom, a lower alkenyl group or a group of -Q.sup.3-A.sup.3 (R.sup.1d)R.sup.1e; A.sup.3 is a nitrogen atom, or is a methine or 1-vinyl-2-ylidene group optionally substituted by a hydroxyl group, a lower alkyl group or a hydroxy-lower alkyl group; Q.sup.3 is a single bond or a lower alkylene group, wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a sulfur atom, a carbonyl group, a sulfinyl group or a sulfonyl group, and/or substituted by a halogen atom, a cyano group, a hydroxyl group or a lower alkyl group; R.sup.1d is a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a lower alkyl group or a hydroxy-lower alkyl group, R.sup.1e is a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a lower alkyl group or a hydroxy-lower alkyl group, or R.sup.1d and R.sup.1e together form a lower alkylene group wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, a carbonyl group, a vinylene group or a group of --N(R.sup.1f)--, or substituted by a hydroxyl group or a lower alkyl group; R.sup.1f is a hydrogen atom, a lower alkyl group, a halo-lower alkyl group, a lower alkenyl group or a lower alkanoyl group; R.sup.5 is a hydrogen atom, a halogen atom, a lower alkyl group, a halo-lower alkyl group, a hydroxy-lower alkyl group, a lower alkoxy group, a lower alkanoyl group, a hydroxy-lower alkylamino group, a carbamoyl group or a hydroxy-lower alkylcarbamoyl group; R.sup.6 is a hydrogen atom, a halogen atom, a lower alkyl group, a halo-lower alkyl group, a hydroxy-lower alkyl group, a lower alkoxy group, a lower alkanoyl group, a hydroxy-lower alkylamino group, a carbamoyl group or a hydroxy-lower alkylcarbamoyl group; R.sup.10 is a lower alkenyl group, which is optionally substituted with a halogen atom; R.sup.20 is an aryl group or a heteroaromatic group, which is optionally substituted with a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a carboxyl group, a group of -Q.sup.4-A.sup.4(R.sup.1g)R.sup.1h and a group of -Q.sup.5-Ar.sup.a; A.sup.4 is a nitrogen atom, or is a methine group optionally substituted by a halogen atom, a hydroxyl group, a lower alkyl group or a hydroxy-lower alkyl group; Ar.sup.a is an aryl group or a heteroaromatic group, which is optionally substituted with a substituent selected from a group consisting of a halogen atom, a lower alkyl group, a halo-lower alkyl group, a hydroxy-lower alkyl group and a lower alkoxy group; Q.sup.4 is a single bond or a lower alkylene group, wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom or a carbonyl group, or substituted by a lower alkyl group; Q.sup.5 is a single bond, an oxygen atom, a sulfur atom, a carbonyl group or a lower alkylene group, wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a sulfur atom or a carbonyl group, or substituted by a halogen atom or a lower alkyl group; R.sup.1g is a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a lower alkyl group, a lower alkoxy-lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group or a lower alkylsulfonyl group, R.sup.1h is a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a lower alkyl group, a lower alkoxy-lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group or a lower alkylsulfonyl group, or R.sup.1g and R.sup.1h together form a lower alkylene group, wherein one or two or more methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, a carbonyl group or a group of --N(R.sup.1i)--, or substituted by a halogen atom or a lower alkyl group; R.sup.1i is a hydrogen atom, a lower alkyl group or a halo-lower alkyl group. 3. The compound as claimed in claim 2, or a salt thereof, wherein R.sup.10 is an allyl group, a 2-methyl-2-propenyl group or a 3-methyl-2-butenyl group. 4. The compound as claimed in claim 2, or a salt thereof, wherein R.sup.20 is a phenyl group, a thienyl group, a pyrazolyl group or a pyridyl group, which is optionally substituted with a substituent selected from a group consisting of a halogen atom, a cyano group, a nitro group, a carboxyl group, a group of -Q.sup.4-A.sup.4(R.sup.1g)R.sup.1h and a group of -Q.sup.5-Ar.sup.a. 5. The compound as claimed in claim 2, or a salt thereof, wherein R.sup.20 is a phenyl or pyridyl group having a group of -Q.sup.4-A.sup.4(R.sup.1g)R.sup.1h. 6. The compound as claimed in claim 2, or a salt thereof, wherein in the group of the formula -Q.sup.1-A.sup.1-Q.sup.2-A.sup.2(R.sup.1a)R.sup.1b, (i) A.sup.1, Q.sup.1 and Q.sup.2 are a single bond, A.sup.2 is a nitrogen atom, and R.sup.1a and R.sup.1b together form a lower alkylene group wherein one or two methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a sulfonyl group, a carbonyl group or a group of --N(R.sup.1c)--, or substituted by a hydroxyl group; (ii) A.sup.1, Q.sup.1 and Q.sup.2 are a single bond, A.sup.2 is a methine or 1-vinyl-2-ylidene group optionally substituted by a hydroxyl group, and R.sup.1a and R.sup.1b together form a lower alkylene group wherein one methylene group constituting the lower alkylene group is replaced by a group of --N(R.sup.1c)--; (iii) A.sup.1 is an oxygen atom, A.sup.2 is a methine group, Q.sup.1 and Q.sup.2 are a single bond, and R.sup.1a and R.sup.1b together form a lower alkylene group wherein one methylene group constituting the lower alkylene group is replaced by a group of --N(R.sup.1c)--; (iv) A.sup.1 is an oxygen atom, A.sup.2 is a nitrogen atom, Q.sup.1 is a single bond, Q.sup.2 is an ethylene group, R.sup.1a is a lower alkyl group, and R.sup.1b is a lower alkyl group; or (v) A.sup.1 and Q.sup.2 are a single bond, A.sup.2 is a nitrogen atom, Q.sup.1 is a methylene group, R.sup.1a is a lower alkyl group, and R.sup.1b is a lower alkyl group. 7. The compound as claimed in claim 2, or a salt thereof, wherein R.sup.20 is a phenyl or pyridyl group having a group of -Q.sup.4-A.sup.4(R.sup.1g)R.sup.1h, and the group of -Q.sup.1-A.sup.1-Q.sup.2-A.sup.2(R.sup.1a)R.sup.1b is selected from the formula (aa1'): ##STR00218## 8. The compound as claimed in claim 6, or a salt thereof, wherein R.sup.1c is a hydrogen atom or a group of -Q.sup.3-A.sup.3(R.sup.1d)R.sup.1e, and in the group of -Q.sup.3-A.sup.3(R.sup.1d)R.sup.1e; (i) A.sup.3 is a methine group optionally substituted by a hydroxyl group or a lower alkyl group, Q.sup.3 is a single bond, R.sup.1d is a hydrogen atom or a lower alkyl group, and R.sup.1c is a hydrogen atom or a lower alkyl group; (ii) A.sup.3 is a methine group, Q.sup.3 is a single bond or a lower alkylene group, and R.sup.1d and R.sup.1c together form a lower alkylene group wherein one methylene group constituting the lower alkylene group may be replaced by a group of --N(R.sup.1f)--; (iii) A.sup.3 is a methine group optionally substituted with a hydroxyl group or a lower alkyl group, Q.sup.3 is a lower alkylene group wherein one or two methylene groups constituting the lower alkylene group may be independently replaced by an oxygen atom, a carbonyl group or a sulfonyl group, and/or substituted by a hydroxyl group, R.sup.1d is a hydrogen atom, a halogen atom, a cyano group or a lower alkyl group, and R.sup.1e is a hydrogen atom, a halogen atom, a cyano group or a lower alkyl group; or (iv) A.sup.3 is a nitrogen atom, Q.sup.3 is a lower alkylene group wherein one methylene group constituting the lower alkylene group is replaced by a carbonyl group, R.sup.1d-- is a hydrogen atom or a lower alkyl group, and R.sup.1e is a hydrogen atom or a lower alkyl group. 9. The compound as claimed in claim 1, or a salt thereof, which is as follows: 3-(2-allyl-6-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-3-oxo-1,2- -dihydro-3H-pyrazolo[3,4-d]pyrimidin-1-yl)-N,N-dimethylbenzamide, 2-allyl-1-[3-(1-hydroxy-1-methylethyl)phenyl]-6-{[4-(4-methylpiperazin-1-- yl)phenyl]amino}-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, 2-allyl-1-[3-(dimethylaminomethyl)phenyl]-6-{[4-(4-methylpiperazin-1-yl)p- henyl]amino}-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, 2-allyl-6-{[3-hydroxymethyl-4-(4-methylpiperazin-1-yl)phenyl]amino}-1-pyr- idin-2-yl-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, 2-allyl-1-(6-aminopyridin-2-yl)-6-{4-(4-methylpiperazin-1-yl)phenyl]amino- }-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, 2-allyl-1-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]-6-{[4-(4-methylpipera- zin-1-yl)phenyl]amino}-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, 2-allyl-6-{[4-(4-ethylpiperazin-1-yl)phenyl]amino}-1-[6-(1-hydroxy-1-meth- ylethyl)pyridin-2-yl]-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, 6-{[4-(4-acetylpiperazin-1-yl)phenyl]amino}-2-allyl-1-[6-(1-hydroxy-1-met- hylethyl)pyridin-2-yl]-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, 2-allyl-6-({4-[4-(2-hydroxyethyl)piperazin-1-yl]phenyl}amino)-1-[6-(1-hyd- roxy-1-methylethyl)pyridin-2-yl]-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3- -one, 2-allyl-1-[6-(2-hydroxy-2-methylpropyl)pyridin-2-yl]-6-{[4-(1-methyl- piperidin-4-yl)phenyl]amino}-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one- , 2-allyl-6-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-1-[6-(2-oxopyrrolidi- n-1-yl)pyridin-2-yl]-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, N-{[6-(2-allyl-6-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-3-oxo-1,2-dihy- dro-3H-pyrazolo[3,4-d]pyrimidin-1-yl)pyridin-2-yl]methyl}-N-methylmethanes- ulfonamide. 10. The compound as claimed in claim 1, or a salt thereof, which is 3-(2-allyl-6-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-3-oxo-1,2-dihydro-- 3H-pyrazolo[3,4-d]pyrimidin-1-yl)-N,N-dimethylbenzamide. 11. The compound as claimed in claim 1, or a salt thereof, which is 2-allyl-6-{[3-(hydroxymethyl)-4-(4-methylpiperazin-1-yl)phenyl]amino}-1-(- 3-thienyl)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one. 12. The compound as claimed in claim 1, or a salt thereof, which is 2-allyl-1-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]-6-{[4-(4-methylpipera- zin-1-yl)phenyl]amino}-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one. 13. The compound as claimed in claim 1, or a salt thereof, which is 2-allyl-1-[6-(3-methyl-2-oxoimidazolidin-1-yl)pyridin-2-yl]-6-{[4-(4-meth- ylpiperazin-1-yl)phenyl]amino}-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-o- ne. 14. A pharmaceutical composition comprising a therapeutically-effective amount of the compound as claimed in claim 1, or a salt thereof, and a pharmaceutically acceptable carrier or diluent. 15. A pharmaceutical composition comprising: (a) a preparation comprising, together with a pharmaceutically acceptable carrier or diluent, the compound of above formula (I) or a pharmaceutically acceptable salt thereof; and (b) a preparation comprising, together with a pharmaceutically acceptable carrier or diluent, one anticancer agent selected from the group consisting of anticancer alkylating agents, anticancer antimetabolites, anticancer antibiotics, plant-derived anticancer agents, anticancer platinum-coordinated complex compounds, anticancer camptothecin derivatives, anticancer tyrosine kinase inhibitors, monoclonal antibodies, interferons, biological response modifiers, and other anticancer agents or a pharmaceutically acceptable salt thereof, wherein: the anticancer alkylating agents are selected from the group consisting of nitrogen mustard N-oxide, cyclophosphamide, ifosfamide, melphalan, busulfan, mitobronitol, carboquone, thiotepa, ranimustine, nimustine, temozolomide, and carmustine; the anticancer antimetabolites are selected from the group consisting of methotrexate, 6-mercaptopurine riboside, mercaptopurine, 5-fluorouracil, tegafur, doxifluridine, carmofur, cytarabine, cytarabine ocfosfate, enocitabine, S-1, gemcitabine, fludarabine, and pemetrexed disodium; the anticancer antibiotics are selected from the group consisting of actinomycin D, doxorubicin, daunorubicin, neocarzinostatin, bleomycin, peplomycin, mitomycin C, aclarubicin, pirarubicin, epirubicin, zinostatin stimalamer, idarubicin, sirolimus, and valrubicin; the plant-derived anticancer agents are selected from the group consisting of vincristine, vinblastine, vindeshine, etoposide, sobuzoxane, docetaxel, paclitaxel, and vinorelbine; the anticancer platinum-coordinated complex compounds are selected from the group consisting of cisplatin, carboplatin, nedaplatin, and oxaliplatin; the anticancer camptothecin derivatives are selected from the group consisting of irinotecan, topotecan, and camptothecin; the anticancer tyrosine kinase inhibitors are selected from the group consisting of gefitinib, imatinib, and erlotinib; the monoclonal antibodies are selected from the group consisting of cetuximab, bevacizumab, rituximab, bevacizumab, alemtuzumab, and trastuzumab; the interferons are selected from the group consisting of interferon .alpha., interferon .alpha.-2a, interferon .alpha.-2b, interferon .beta., interferon .gamma.-1a, and interferon .alpha.-n1, the biological response modifiers are selected from the group consisting of krestin, lentinan, sizofuran, picibanil, or ubenimex, and the other anticancer agents are selected from the group consisting of mitoxantrone, L-asparaginase, procarbazine, dacarbazine, hydroxycarbamide, pentostatin, tretinoin, alefacept, darbepoetin alfa, anastrozole, exemestane, bicalutamide, leuprorelin, flutamide, fulvestrant, pegaptanib octasodium, denileukin diftitox, aldesleukin, thyrotropin alfa, arsenic trioxide, bortezomib, capecitabine, and goserelin. |
Details for Patent 7,834,019
Applicant | Tradename | Biologic Ingredient | Dosage Form | BLA | Approval Date | Patent No. | Expiredate |
---|---|---|---|---|---|---|---|
Genzyme Corporation | THYROGEN | thyrotropin alfa | For Injection | 020898 | 11/30/1998 | ⤷ Try a Trial | 2026-04-27 |
Recordati Rare Diseases, Inc. | ELSPAR | asparaginase | For Injection | 101063 | 01/10/1978 | ⤷ Try a Trial | 2026-04-27 |
Clinigen, Inc. | PROLEUKIN | aldesleukin | For Injection | 103293 | 05/05/1992 | ⤷ Try a Trial | 2026-04-27 |
Genentech, Inc. | RITUXAN | rituximab | Injection | 103705 | 11/26/1997 | ⤷ Try a Trial | 2026-04-27 |
Idec Pharmaceuticals Corp. | RITUXAN | rituximab | Injection | 103737 | 02/19/2002 | ⤷ Try a Trial | 2026-04-27 |
Eisai, Incorporated | ONTAK | denileukin diftitox | Injection | 103767 | 02/05/1999 | ⤷ Try a Trial | 2026-04-27 |
>Applicant | >Tradename | >Biologic Ingredient | >Dosage Form | >BLA | >Approval Date | >Patent No. | >Expiredate |
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