CA2192824C - Pyridone-carboxylic acid derivatives, processes for the preparation thereof and anti-tumor agents containing the pyridone-carboxylic acid derivatives - Google Patents
Pyridone-carboxylic acid derivatives, processes for the preparation thereof and anti-tumor agents containing the pyridone-carboxylic acid derivatives Download PDFInfo
- Publication number
- CA2192824C CA2192824C CA002192824A CA2192824A CA2192824C CA 2192824 C CA2192824 C CA 2192824C CA 002192824 A CA002192824 A CA 002192824A CA 2192824 A CA2192824 A CA 2192824A CA 2192824 C CA2192824 C CA 2192824C
- Authority
- CA
- Canada
- Prior art keywords
- group
- carboxylic acid
- amino
- oxo
- hydrogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 34
- YSLIPUSJNFIFAB-UHFFFAOYSA-N 2-oxopyridine-1-carboxylic acid Chemical class OC(=O)N1C=CC=CC1=O YSLIPUSJNFIFAB-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title abstract description 30
- 239000002246 antineoplastic agent Substances 0.000 title abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 194
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 125000005843 halogen group Chemical group 0.000 claims abstract description 45
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 22
- -1 2-(1-piperidinyl)ethyl Chemical group 0.000 claims description 75
- 239000000243 solution Substances 0.000 claims description 65
- 239000002904 solvent Substances 0.000 claims description 54
- 206010028980 Neoplasm Diseases 0.000 claims description 45
- 241000282414 Homo sapiens Species 0.000 claims description 37
- 201000011510 cancer Diseases 0.000 claims description 29
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 125000000539 amino acid group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 238000011321 prophylaxis Methods 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 11
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 11
- 150000001413 amino acids Chemical class 0.000 claims description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 229910052731 fluorine Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
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- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- XZAFZXJXZHRNAQ-CHWSQXEVSA-N 7-[(3r,4r)-3-methoxy-4-(methylamino)pyrrolidin-1-yl]-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carboxylic acid Chemical compound C1[C@@H](OC)[C@H](NC)CN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC=CN=3)C2=N1 XZAFZXJXZHRNAQ-CHWSQXEVSA-N 0.000 claims description 4
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- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
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- VVVWHMHKCFDWCZ-UHFFFAOYSA-N 5-amino-7-(3-aminopyrrolidin-1-yl)-1-(4-fluoro-1,3-thiazol-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(N)CCN1C1=CC(N)=C2C(=O)C(C(O)=O)=CN(C=3SC=C(F)N=3)C2=N1 VVVWHMHKCFDWCZ-UHFFFAOYSA-N 0.000 claims description 2
- GYYDYDAZUSQQPK-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-(4,5-difluoro-1,3-thiazol-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(N)CCN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC(F)=C(F)N=3)C2=N1 GYYDYDAZUSQQPK-UHFFFAOYSA-N 0.000 claims description 2
- WBFCJQINHUSUBY-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-(4-chloro-1,3-thiazol-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(N)CCN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC=C(Cl)N=3)C2=N1 WBFCJQINHUSUBY-UHFFFAOYSA-N 0.000 claims description 2
- PDFNXFJHJSFAIK-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(N)CCN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC=C(N=3)C=3C=C(F)C(F)=CC=3)C2=N1 PDFNXFJHJSFAIK-UHFFFAOYSA-N 0.000 claims description 2
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- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 20
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 3
- 125000004185 ester group Chemical group 0.000 claims 3
- 125000005633 phthalidyl group Chemical group 0.000 claims 3
- 208000032839 leukemia Diseases 0.000 claims 2
- VUIVREUKHPUJLP-UHFFFAOYSA-N 7-(3-amino-4-fluoropyrrolidin-1-yl)-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(F)C(N)CN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC=CN=3)C2=N1 VUIVREUKHPUJLP-UHFFFAOYSA-N 0.000 claims 1
- REONEPLTLHJEFU-UHFFFAOYSA-N 7-(3-amino-4-methoxy-3-methylpyrrolidin-1-yl)-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(N)(C)C(OC)CN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC=CN=3)C2=N1 REONEPLTLHJEFU-UHFFFAOYSA-N 0.000 claims 1
- OQLXRHQFNBYXAC-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-4-oxo-1-[4-(trifluoromethyl)-1,3-thiazol-2-yl]-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(N)CCN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC=C(N=3)C(F)(F)F)C2=N1 OQLXRHQFNBYXAC-UHFFFAOYSA-N 0.000 claims 1
- DTBUZJLBDOCRKE-UHFFFAOYSA-N 7-(4-amino-3-methoxy-3-methylpyrrolidin-1-yl)-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(N)C(OC)(C)CN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC=CN=3)C2=N1 DTBUZJLBDOCRKE-UHFFFAOYSA-N 0.000 claims 1
- XZAFZXJXZHRNAQ-QWHCGFSZSA-N 7-[(3r,4s)-3-methoxy-4-(methylamino)pyrrolidin-1-yl]-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carboxylic acid Chemical compound C1[C@@H](OC)[C@@H](NC)CN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC=CN=3)C2=N1 XZAFZXJXZHRNAQ-QWHCGFSZSA-N 0.000 claims 1
- CUPMXLHWKJNXID-UHFFFAOYSA-N 7-[3-amino-3-(fluoromethyl)pyrrolidin-1-yl]-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(N)(CF)CCN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC=CN=3)C2=N1 CUPMXLHWKJNXID-UHFFFAOYSA-N 0.000 claims 1
- DCSAWHIPFYGGDP-UHFFFAOYSA-N 7-[3-amino-4-(fluoromethyl)pyrrolidin-1-yl]-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(CF)C(N)CN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC=CN=3)C2=N1 DCSAWHIPFYGGDP-UHFFFAOYSA-N 0.000 claims 1
- LKOBGWDBTDWWGK-UHFFFAOYSA-N 7-[3-amino-4-(trifluoromethyl)pyrrolidin-1-yl]-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(C(F)(F)F)C(N)CN1C1=CC=C2C(=O)C(C(O)=O)=CN(C=3SC=CN=3)C2=N1 LKOBGWDBTDWWGK-UHFFFAOYSA-N 0.000 claims 1
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- 230000004083 survival effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 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 1
- SMHLDHOMHQKVDQ-RKDXNWHRSA-N tert-butyl 2-[[(3s,4r)-4-methylpyrrolidin-3-yl]amino]acetate Chemical compound C[C@@H]1CNC[C@H]1NCC(=O)OC(C)(C)C SMHLDHOMHQKVDQ-RKDXNWHRSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DQQJBEAXSOOCPG-UHFFFAOYSA-N tert-butyl n-pyrrolidin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNC1 DQQJBEAXSOOCPG-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 239000012929 tonicity agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960004799 tryptophan Drugs 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
- 239000004474 valine Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15657894 | 1994-06-14 | ||
| JP156578/1994 | 1994-06-14 | ||
| JP19792194 | 1994-07-28 | ||
| JP197921/1994 | 1994-07-28 | ||
| JP30691494 | 1994-11-15 | ||
| JP306914/1994 | 1994-11-15 | ||
| JP339956/1994 | 1994-12-28 | ||
| JP33995694 | 1994-12-28 | ||
| JP81705/1995 | 1995-03-13 | ||
| JP8170595 | 1995-03-13 | ||
| PCT/JP1995/001110 WO1995034559A1 (en) | 1994-06-14 | 1995-06-06 | Novel compound, process for producing the same, and antitumor agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2192824A1 CA2192824A1 (en) | 1995-12-21 |
| CA2192824C true CA2192824C (en) | 2006-11-07 |
Family
ID=27524935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002192824A Expired - Lifetime CA2192824C (en) | 1994-06-14 | 1995-06-06 | Pyridone-carboxylic acid derivatives, processes for the preparation thereof and anti-tumor agents containing the pyridone-carboxylic acid derivatives |
Country Status (26)
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA04002136A (es) | 2001-09-26 | 2005-03-07 | Bayer Pharmaceuticals Corp | Derivados de 1,6-naftiridina y su uso para el tratamiento de la diabetes y trastornos relacionados. |
| US6802423B2 (en) * | 2002-02-20 | 2004-10-12 | Trans Global Foods, Inc. | Disposable food delivery apparatus |
| WO2004091627A2 (en) * | 2003-04-07 | 2004-10-28 | Cylene Pharmaceuticals, Inc. | Heterocyclic substituted 1,4-dihydro-4-oxo-1,8-naphthpyridine analogs |
| AU2004272414B2 (en) * | 2003-09-10 | 2009-05-28 | Kyorin Pharmaceutical Co., Ltd. | 7-(4-substituted 3- cyclopropylaminomethyl-1- pyrrolidinyl) quinolonecarboxylic acid derivative |
| DE10352979A1 (de) * | 2003-11-13 | 2005-06-09 | Merck Patent Gmbh | Pyridopyrimidinone |
| AU2013201203C1 (en) * | 2004-03-15 | 2015-04-23 | Sumitomo Dainippon Pharma Co., Ltd. | Sns-595 and methods of using the same |
| AU2005222607B2 (en) * | 2004-03-15 | 2010-11-25 | Sunesis Pharmaceuticals, Inc. | SNS-595 and methods of using the same |
| RU2405781C2 (ru) * | 2004-10-14 | 2010-12-10 | Ф.Хоффманн-Ля Рош Аг | 1, 5-нафтиридиназолидиноны, обладающие cdk1 антипролиферативной активностью |
| US7501428B2 (en) * | 2004-10-14 | 2009-03-10 | Hoffmann-La Roche Inc. | Quinazoline thiazolinones |
| RU2420524C2 (ru) * | 2005-05-19 | 2011-06-10 | Дайити Санкио Компани, Лимитед | Производные три- или тетра-замещенного-3-аминопирролидина |
| US7563805B2 (en) * | 2005-05-19 | 2009-07-21 | Daiichi Pharmaceutical Co., Ltd. | Tri-, tetra-substituted-3-aminopyrrolidine derivative |
| CA2619663A1 (en) * | 2005-08-19 | 2007-02-22 | Cylene Pharmaceuticals, Inc. | Human ribosomal dna(rdna) and ribosomal rna (rrna) nucleic acids and uses thereof |
| CN104873502A (zh) * | 2005-09-02 | 2015-09-02 | 逊尼希思制药公司 | 使用(+)-1,4-二氢-7-[(3s,4s)-3-甲氧基-4-(甲氨基)-1-吡咯烷基]-4-氧代-1-(2-噻唑基)-1,8-萘啶-3-羧酸治疗癌症的方法 |
| KR20080041298A (ko) * | 2005-09-02 | 2008-05-09 | 선에시스 파마슈티컬스 인코포레이티드 | 암 치료를 위한(＋)-1,4-디히드로-7-[(3ｓ,4ｓ)-3-메톡시-4-(메틸아미노)-1-피롤리디닐]-4-옥소-1-(2-티아졸릴)-1,8-나프티리딘-3-카르복실산의 사용 방법 |
| KR20170118936A (ko) * | 2005-09-02 | 2017-10-25 | 선에시스 파마슈티컬스 인코포레이티드 | 암 치료를 위한 (＋)-1,4-디히드로-7-［(3ｓ,4ｓ)-3-메톡시-4-(메틸아미노)-1-피롤리디닐］-4-옥소-1-(2-티아졸릴)-1,8-나프티리딘-3-카르복실산의 사용 방법 |
| AU2013219242C1 (en) * | 2005-09-02 | 2016-09-22 | Sunesis Pharmaceuticals, Inc. | Methods of using (+)-1,4-dihydro-7-[(3s,4s)-3-methoxy-4-(methylamino)-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid for treatment of cancer |
| US8580814B2 (en) * | 2006-04-03 | 2013-11-12 | Sunesis Pharmaceuticals, Inc. | Methods of using (+)-1,4-dihydro-7-[(3S,4S)-3-methoxy-4-(methylamino)-1-pyrrolidinyl]-4- oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid for treatment of cancer |
| RU2428983C2 (ru) * | 2005-09-02 | 2011-09-20 | Санесис Фармасьютикалз, Инк. | Способы применения (+)-1,4-дигидро-7-[(3s,4s)-3-метокси-4-(метиламино)-1-пирролидинил]-4-оксо-1-(2-тиазолил)-1,8-нафтиридин-3-карбоновой кислоты для лечения рака |
| CN101305000A (zh) * | 2005-09-14 | 2008-11-12 | 詹森药业有限公司 | 作为c-fms激酶抑制剂的5-氧代-5,8-二氢-吡啶并-嘧啶类 |
| TW200800983A (en) | 2005-09-14 | 2008-01-01 | Janssen Pharmaceutica Nv | 5-oxo-5,8-dihydro-pyrido-pyrimidines as inhibitors of C-FMS kinase |
| US7642270B2 (en) | 2005-09-14 | 2010-01-05 | Janssen Pharmaceutica N.V. | 5-oxo-5,8-dihydro-pyrido-pyrimidine as inhibitors of c-fms kinase |
| US8124773B2 (en) | 2006-06-12 | 2012-02-28 | Sunesis Pharmaceuticals, Inc. | 1,8-naphthyridine compounds for the treatment of cancer |
| US20100048609A1 (en) * | 2006-08-01 | 2010-02-25 | Jacobs Jeffrey W | Pharmaceutical dosage forms for (+)-1,4-dihydro-7-[(3s,4s)-3-methoxy-4-(methylamino)-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid |
| DK2049109T3 (en) * | 2006-08-02 | 2016-01-11 | Sunesis Pharmaceuticals Inc | Combined use of (+) - 1,4-dihydro-7 - [(3S, 4S) -3-methoxy-4- (methylamino) -1-pyrrolidinyl] -4-oxo-1- (2-thiazolyl) -1,8-naphthyridine-3-carboxylic acid and cytarabine (Ara-C) for the treatment of leukemia |
| MX2010004350A (es) * | 2007-10-22 | 2010-05-19 | Sunesis Pharmaceuticals Inc | Metodos de uso del acido (+)-1,4-dihidro-7-[(3s,4s)]-3-metoxi-4-(m etilamino)-1-pirrolidinil-4-oxo-1-(2-tiazolil)-1, 8-naftiridina-3-carboxilico en terapias de combinacion. |
| AU2008335772B2 (en) | 2007-12-10 | 2014-11-27 | Sunesis Pharmaceuticals, Inc. | Methods of using (+)-1,4-dihydro-7-[(3S,4S)-3- methoxy-4-(methylamino)-1-pyrrolidinyl]-4-oxo-1- (2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid for treatment of antecedent hematologic disorders |
| KR20170090535A (ko) | 2008-12-31 | 2017-08-07 | 선에시스 파마슈티컬스 인코포레이티드 | (＋)-1,4-다이하이드로-7-［(3ｓ,4ｓ)-3-메톡시-4-(메틸아미노)-1-피롤리딘일］-4-옥소-1-(2-티아졸릴)-1,8-나프티리딘-3-카복실산의 제조 방법 |
| RU2558835C2 (ru) | 2009-02-27 | 2015-08-10 | Санесис Фармасьютикалз, Инк. | Способы применения sns-595 для лечения субъектов с онкологическими заболеваниями, имеющих сниженную активность brca2 |
| UA110465C2 (en) * | 2009-09-04 | 2016-01-12 | Sunesis Pharmaceutecals Inc | Stable sns-595 composition |
| US8470817B2 (en) * | 2009-10-26 | 2013-06-25 | Sunesis Pharmaceuticals, Inc. | Compounds and methods for treatment of cancer |
| BR112013029201B1 (pt) | 2011-05-13 | 2022-08-09 | Array Biopharma Inc | Compostos de pirrolidinil ureia e pirrolidinil tioureia, seu processo de preparação, seu uso e composições farmacêuticas |
| CN103497186B (zh) * | 2013-09-24 | 2015-02-25 | 浙江司太立制药股份有限公司 | 含有烷氧亚氨基取代的萘啶酮羧酸衍生物及其制备方法 |
| AU2018238079B2 (en) * | 2017-03-24 | 2022-03-03 | Wakunaga Pharmaceutical Co., Ltd. | Novel pyridone carboxylic acid derivative or salt thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3988463A (en) * | 1974-05-06 | 1976-10-26 | Merck & Co., Inc. | Method of preventing metastasis of H. Ep. No. 3 |
| US4384001A (en) * | 1978-12-21 | 1983-05-17 | Gosalvez Mario | Treatment of tumors with thiazolidine-4-carboxylic acid |
| US4730000A (en) * | 1984-04-09 | 1988-03-08 | Abbott Laboratories | Quinoline antibacterial compounds |
| EP0154780B1 (en) * | 1984-01-26 | 1990-04-11 | Abbott Laboratories | Quinoline antibacterial compounds |
| NZ210847A (en) * | 1984-01-26 | 1988-02-29 | Abbott Lab | Naphthyridine and pyridopyrimidine derivatives and pharmaceutical compositions |
| JPS61152682A (ja) * | 1984-12-27 | 1986-07-11 | Dainippon Pharmaceut Co Ltd | ピリドンカルボン酸誘導体、そのエステルおよびその塩 |
| JPS61251667A (ja) * | 1985-04-30 | 1986-11-08 | Otsuka Pharmaceut Co Ltd | ベンゾヘテロ環化合物 |
| NZ216519A (en) * | 1985-06-13 | 1989-02-24 | Schering Corp | Polycyclic compounds and pharmaceutical compositions |
| EP0226624A1 (en) * | 1985-06-14 | 1987-07-01 | The Upjohn Company | Cyclopentapyrazole and tetrahydroindazole compounds |
| JPS6233176A (ja) * | 1985-08-05 | 1987-02-13 | Toyama Chem Co Ltd | １，４−ジヒドロ−４−オキソナフチリジン誘導体およびその塩 |
| JP2704428B2 (ja) * | 1988-06-15 | 1998-01-26 | 富山化学工業株式会社 | キノロンカルボン酸誘導体またはその塩 |
| DE3906365A1 (de) * | 1988-07-15 | 1990-01-18 | Bayer Ag | 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
| JPH06233176A (ja) * | 1993-01-29 | 1994-08-19 | Sony Corp | ビデオカメラ |
-
1995
- 1995-06-06 RO RO96-02349A patent/RO117793B1/ro unknown
- 1995-06-06 AT AT95920265T patent/ATE209645T1/de active
- 1995-06-06 SI SI9530567T patent/SI0787726T1/xx unknown
- 1995-06-06 KR KR1019960707029A patent/KR100350921B1/ko not_active Expired - Lifetime
- 1995-06-06 SK SK1574-96A patent/SK281341B6/sk not_active IP Right Cessation
- 1995-06-06 CZ CZ19963643A patent/CZ292631B6/cs not_active IP Right Cessation
- 1995-06-06 HU HU9603455A patent/HU220072B/hu unknown
- 1995-06-06 AU AU25767/95A patent/AU679859B2/en not_active Expired
- 1995-06-06 NZ NZ287139A patent/NZ287139A/en not_active IP Right Cessation
- 1995-06-06 MX MX9606331A patent/MX9606331A/es unknown
- 1995-06-06 CA CA002192824A patent/CA2192824C/en not_active Expired - Lifetime
- 1995-06-06 BR BR9508037A patent/BR9508037A/pt not_active IP Right Cessation
- 1995-06-06 ES ES95920265T patent/ES2163512T3/es not_active Expired - Lifetime
- 1995-06-06 RU RU97100718/04A patent/RU2151770C1/ru active
- 1995-06-06 EP EP95920265A patent/EP0787726B1/en not_active Expired - Lifetime
- 1995-06-06 CN CN95194461A patent/CN1053668C/zh not_active Expired - Lifetime
- 1995-06-06 PT PT95920265T patent/PT787726E/pt unknown
- 1995-06-06 US US08/765,232 patent/US5817669A/en not_active Expired - Lifetime
- 1995-06-06 JP JP50192396A patent/JP3391796B2/ja not_active Expired - Lifetime
- 1995-06-06 PL PL95317726A patent/PL181867B1/pl unknown
- 1995-06-06 DE DE69524251T patent/DE69524251T2/de not_active Expired - Lifetime
- 1995-06-06 DK DK95920265T patent/DK0787726T3/da active
- 1995-06-06 WO PCT/JP1995/001110 patent/WO1995034559A1/ja not_active Ceased
- 1995-06-13 TW TW084106000A patent/TW319769B/zh not_active IP Right Cessation
-
1996
- 1996-12-11 NO NO965305A patent/NO307255B1/no not_active IP Right Cessation
- 1996-12-13 FI FI965020A patent/FI112485B/fi not_active IP Right Cessation
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