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Last Updated: March 29, 2024

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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