JPS57167974A - Preparation of 4-phenylphthalazine derivative - Google Patents
Preparation of 4-phenylphthalazine derivativeInfo
- Publication number
- JPS57167974A JPS57167974A JP5244681A JP5244681A JPS57167974A JP S57167974 A JPS57167974 A JP S57167974A JP 5244681 A JP5244681 A JP 5244681A JP 5244681 A JP5244681 A JP 5244681A JP S57167974 A JPS57167974 A JP S57167974A
- Authority
- JP
- Japan
- Prior art keywords
- derivative
- phosphorus
- alkylcarbonyl
- alkoxycarbonyl
- carboxyl
- 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.)
- Granted
Links
- KHIILJVSYUGMSE-UHFFFAOYSA-N 1-phenylphthalazine Chemical class C1=CC=CC=C1C1=NN=CC2=CC=CC=C12 KHIILJVSYUGMSE-UHFFFAOYSA-N 0.000 title 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- XCJLBNVENUPHEA-UHFFFAOYSA-N 4-phenyl-2h-phthalazin-1-one Chemical class C12=CC=CC=C2C(=O)NN=C1C1=CC=CC=C1 XCJLBNVENUPHEA-UHFFFAOYSA-N 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 150000003464 sulfur compounds Chemical class 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 210000001772 blood platelet Anatomy 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
PURPOSE: To obtain the titled compound having improved inhibiting action on blood platelet aggregation through one process, by reacting 4-phenyl-1(2H)-phthalazinone derivative with aniline or its derivative in the presence of a phosphorus or sulfur compound.
CONSTITUTION: A 4-phenyl-1(2H)-phthalazinone derivative shown by the formulaI (R2 and R3 are alkyl, alkoxy, halogen, alkoxycarbonyl, carboxyl, alkylcarbonyl, hydroxyl, trifluoromethyl; m and n are 0W3) is reacted with an aniline shown by the formula II (R1 is alkyl, alkoxy, halogen, alkoxycarbonyl, carboxyl, cyano, alkylcarbonyl, hydroxyl, CF3; l is 0W3) or its derivative in the presence of a phosphorus or sulfur compound (e.g., phosphorus oxychloride, sulfuryl chloride, etc.) to give the desired compound shown by the formula III.
USE: A synthetic intermediate, etc.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5244681A JPS57167974A (en) | 1981-04-09 | 1981-04-09 | Preparation of 4-phenylphthalazine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5244681A JPS57167974A (en) | 1981-04-09 | 1981-04-09 | Preparation of 4-phenylphthalazine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57167974A true JPS57167974A (en) | 1982-10-16 |
| JPH0329791B2 JPH0329791B2 (en) | 1991-04-25 |
Family
ID=12914950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5244681A Granted JPS57167974A (en) | 1981-04-09 | 1981-04-09 | Preparation of 4-phenylphthalazine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57167974A (en) |
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5324727A (en) * | 1991-09-26 | 1994-06-28 | Mitsubishi Chem Ind | 3,6-disubstituted pyridazine derivatives |
| US5696159A (en) * | 1994-08-03 | 1997-12-09 | Cell Pathways, Inc. | Lactone compounds for treating patients with precancerous lesions |
| US5776962A (en) * | 1994-08-03 | 1998-07-07 | Cell Pathways, Inc. | Lactone compounds for treating patient with precancerous lesions |
| US5852035A (en) * | 1997-12-12 | 1998-12-22 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to substituted N- arylmethyl and heterocyclmethyl-1H-pyrazolo (3,4-B) quinolin-4-amines |
| US5874440A (en) * | 1995-06-07 | 1999-02-23 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl pyrimidinone derivatives |
| US5942520A (en) * | 1998-01-27 | 1999-08-24 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells by exposure to substituted N-cycloalkylmethyl-1-H-pyrazolo (3,4-B) quinolone-4 amines |
| US5990117A (en) * | 1998-04-15 | 1999-11-23 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to quinazoline derivatives |
| US6020379A (en) * | 1999-02-19 | 2000-02-01 | Cell Pathways, Inc. | Position 7 substituted indenyl-3-acetic acid derivatives and amides thereof for the treatment of neoplasia |
| US6034099A (en) * | 1998-11-24 | 2000-03-07 | Cell Pathways, Inc. | Method for inhibiting neoplastic lesions by administering 4-(arylmethylene)- 2, 3- dihydro-pyrazol-3-ones |
| US6046206A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having a precancerous lesions with amide quinazoline derivatives |
| US6046199A (en) * | 1998-01-14 | 2000-04-04 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with tetracyclic pyrido[3,4-B]indole derivatives |
| US6046216A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl pyridinone derivatives |
| US6060477A (en) * | 1995-06-07 | 2000-05-09 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl cycloamino pyrimidinone derivatives |
| US6077842A (en) * | 1998-11-24 | 2000-06-20 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with pyrazolopyridylpyridazinone derivatives |
| WO2000044726A1 (en) * | 1999-01-26 | 2000-08-03 | Ono Pharmaceutical Co., Ltd. | 2h-phthalazin-1-one derivatives and drugs comprising these derivatives as the active ingredient |
| US6124303A (en) * | 1998-09-11 | 2000-09-26 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 9-substituted 2-(2-N-aloxyphenyl) purin-6-ones |
| US6130053A (en) * | 1999-08-03 | 2000-10-10 | Cell Pathways, Inc. | Method for selecting compounds for inhibition of neoplastic lesions |
| US6133271A (en) * | 1998-11-19 | 2000-10-17 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure thienopyrimidine derivatives |
| US6156528A (en) * | 1997-05-30 | 2000-12-05 | Cell Pathways, Inc | Methods for using a phosphodiesterase in pharmaceutical screening to identify compounds for treatment of neoplasia |
| US6177471B1 (en) | 1999-01-29 | 2001-01-23 | Cell Pathways, Inc. | Method for treating patients with acne by administering a CGMP-specific PDE inhibitor |
| US6180629B1 (en) | 1998-08-14 | 2001-01-30 | Cell Pathways, Inc. | [4,5]-Fused-1,3-disubstituted-1,2-diazine-6-one derivatives with nitrogen containing substitutents in position one for the treatment of neoplasia |
| US6187779B1 (en) | 1998-11-20 | 2001-02-13 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 2,8-disubstituted quinazoline derivatives |
| US6200771B1 (en) | 1998-10-15 | 2001-03-13 | Cell Pathways, Inc. | Method of using a novel phosphodiesterase in pharmaceutical screeing to identify compounds for treatment of neoplasia |
| US6200980B1 (en) | 1995-06-07 | 2001-03-13 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl purinone derivatives |
| US6232312B1 (en) | 1995-06-07 | 2001-05-15 | Cell Pathways, Inc. | Method for treating patient having precancerous lesions with a combination of pyrimidopyrimidine derivatives and esters and amides of substituted indenyl acetic acides |
| US6262059B1 (en) | 1995-06-07 | 2001-07-17 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with quinazoline derivatives |
| US6268372B1 (en) | 1998-09-11 | 2001-07-31 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 2,9-disubstituted purin-6-ones |
| US6369092B1 (en) | 1998-11-23 | 2002-04-09 | Cell Pathways, Inc. | Method for treating neoplasia by exposure to substituted benzimidazole derivatives |
| US6486155B1 (en) | 1998-11-24 | 2002-11-26 | Cell Pathways Inc | Method of inhibiting neoplastic cells with isoquinoline derivatives |
| US6500610B1 (en) | 1997-05-30 | 2002-12-31 | Cell Pathways, Inc | Methods for identifying compounds for inhibiting of neoplastic lesions, and pharmaceutical compositions containing such compounds |
| US6555547B1 (en) | 2000-02-28 | 2003-04-29 | Cell Pathways, Inc. | Method for treating a patient with neoplasia by treatment with a vinca alkaloid derivative |
| US6569638B1 (en) | 2000-03-03 | 2003-05-27 | Cell Pathways, Inc | Method for screening compounds for the treatment of neoplasia |
| US7115647B2 (en) | 1998-01-14 | 2006-10-03 | Osi Pharmaceuticals, Inc. | Method of inhibiting neoplastic cells with indole derivatives |
-
1981
- 1981-04-09 JP JP5244681A patent/JPS57167974A/en active Granted
Cited By (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5324727A (en) * | 1991-09-26 | 1994-06-28 | Mitsubishi Chem Ind | 3,6-disubstituted pyridazine derivatives |
| US5462941A (en) * | 1991-09-26 | 1995-10-31 | Mitsubishi Chemical Corporation | 3,6-disubstituted pyradazine derivatives |
| US5696159A (en) * | 1994-08-03 | 1997-12-09 | Cell Pathways, Inc. | Lactone compounds for treating patients with precancerous lesions |
| US5776962A (en) * | 1994-08-03 | 1998-07-07 | Cell Pathways, Inc. | Lactone compounds for treating patient with precancerous lesions |
| US6200980B1 (en) | 1995-06-07 | 2001-03-13 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl purinone derivatives |
| US5874440A (en) * | 1995-06-07 | 1999-02-23 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl pyrimidinone derivatives |
| US6060477A (en) * | 1995-06-07 | 2000-05-09 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl cycloamino pyrimidinone derivatives |
| US6232312B1 (en) | 1995-06-07 | 2001-05-15 | Cell Pathways, Inc. | Method for treating patient having precancerous lesions with a combination of pyrimidopyrimidine derivatives and esters and amides of substituted indenyl acetic acides |
| US6046206A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having a precancerous lesions with amide quinazoline derivatives |
| US6262059B1 (en) | 1995-06-07 | 2001-07-17 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with quinazoline derivatives |
| US6046216A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl pyridinone derivatives |
| US6156528A (en) * | 1997-05-30 | 2000-12-05 | Cell Pathways, Inc | Methods for using a phosphodiesterase in pharmaceutical screening to identify compounds for treatment of neoplasia |
| US6500610B1 (en) | 1997-05-30 | 2002-12-31 | Cell Pathways, Inc | Methods for identifying compounds for inhibiting of neoplastic lesions, and pharmaceutical compositions containing such compounds |
| US5852035A (en) * | 1997-12-12 | 1998-12-22 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to substituted N- arylmethyl and heterocyclmethyl-1H-pyrazolo (3,4-B) quinolin-4-amines |
| US6046199A (en) * | 1998-01-14 | 2000-04-04 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with tetracyclic pyrido[3,4-B]indole derivatives |
| US7115647B2 (en) | 1998-01-14 | 2006-10-03 | Osi Pharmaceuticals, Inc. | Method of inhibiting neoplastic cells with indole derivatives |
| US5942520A (en) * | 1998-01-27 | 1999-08-24 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells by exposure to substituted N-cycloalkylmethyl-1-H-pyrazolo (3,4-B) quinolone-4 amines |
| US5990117A (en) * | 1998-04-15 | 1999-11-23 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to quinazoline derivatives |
| US6180629B1 (en) | 1998-08-14 | 2001-01-30 | Cell Pathways, Inc. | [4,5]-Fused-1,3-disubstituted-1,2-diazine-6-one derivatives with nitrogen containing substitutents in position one for the treatment of neoplasia |
| US6124303A (en) * | 1998-09-11 | 2000-09-26 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 9-substituted 2-(2-N-aloxyphenyl) purin-6-ones |
| US6268372B1 (en) | 1998-09-11 | 2001-07-31 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 2,9-disubstituted purin-6-ones |
| US6200771B1 (en) | 1998-10-15 | 2001-03-13 | Cell Pathways, Inc. | Method of using a novel phosphodiesterase in pharmaceutical screeing to identify compounds for treatment of neoplasia |
| US6133271A (en) * | 1998-11-19 | 2000-10-17 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure thienopyrimidine derivatives |
| US6187779B1 (en) | 1998-11-20 | 2001-02-13 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 2,8-disubstituted quinazoline derivatives |
| US6369092B1 (en) | 1998-11-23 | 2002-04-09 | Cell Pathways, Inc. | Method for treating neoplasia by exposure to substituted benzimidazole derivatives |
| US6077842A (en) * | 1998-11-24 | 2000-06-20 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with pyrazolopyridylpyridazinone derivatives |
| US6486155B1 (en) | 1998-11-24 | 2002-11-26 | Cell Pathways Inc | Method of inhibiting neoplastic cells with isoquinoline derivatives |
| US6034099A (en) * | 1998-11-24 | 2000-03-07 | Cell Pathways, Inc. | Method for inhibiting neoplastic lesions by administering 4-(arylmethylene)- 2, 3- dihydro-pyrazol-3-ones |
| WO2000044726A1 (en) * | 1999-01-26 | 2000-08-03 | Ono Pharmaceutical Co., Ltd. | 2h-phthalazin-1-one derivatives and drugs comprising these derivatives as the active ingredient |
| US6677333B1 (en) | 1999-01-26 | 2004-01-13 | Ono Pharmaceutical Co., Ltd. | 2H-phthalazin-1-one derivatives and drug containing its derivatives as active ingredient |
| US6177471B1 (en) | 1999-01-29 | 2001-01-23 | Cell Pathways, Inc. | Method for treating patients with acne by administering a CGMP-specific PDE inhibitor |
| US6020379A (en) * | 1999-02-19 | 2000-02-01 | Cell Pathways, Inc. | Position 7 substituted indenyl-3-acetic acid derivatives and amides thereof for the treatment of neoplasia |
| US6130053A (en) * | 1999-08-03 | 2000-10-10 | Cell Pathways, Inc. | Method for selecting compounds for inhibition of neoplastic lesions |
| US6555547B1 (en) | 2000-02-28 | 2003-04-29 | Cell Pathways, Inc. | Method for treating a patient with neoplasia by treatment with a vinca alkaloid derivative |
| US6569638B1 (en) | 2000-03-03 | 2003-05-27 | Cell Pathways, Inc | Method for screening compounds for the treatment of neoplasia |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0329791B2 (en) | 1991-04-25 |
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