DE2237832A1 - Verfahren zur herstellung von 4hydroxymethyl-1-keto-1,2-dihydrophthalazin - Google Patents
Verfahren zur herstellung von 4hydroxymethyl-1-keto-1,2-dihydrophthalazinInfo
- Publication number
- DE2237832A1 DE2237832A1 DE2237832A DE2237832A DE2237832A1 DE 2237832 A1 DE2237832 A1 DE 2237832A1 DE 2237832 A DE2237832 A DE 2237832A DE 2237832 A DE2237832 A DE 2237832A DE 2237832 A1 DE2237832 A1 DE 2237832A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- thrombosis
- formula
- atherosclerosis
- injection
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 18
- SPVIEWHOXUYOPN-UHFFFAOYSA-N 4-(hydroxymethyl)-2h-phthalazin-1-one Chemical compound C1=CC=C2C(CO)=NNC(=O)C2=C1 SPVIEWHOXUYOPN-UHFFFAOYSA-N 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 208000007536 Thrombosis Diseases 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 201000001320 Atherosclerosis Diseases 0.000 claims description 12
- -1 aliphatic alcohols Chemical class 0.000 claims description 11
- 208000032843 Hemorrhage Diseases 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000001802 infusion Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 239000003889 eye drop Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 206010008132 Cerebral thrombosis Diseases 0.000 claims description 3
- 201000001429 Intracranial Thrombosis Diseases 0.000 claims description 3
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- 239000002775 capsule Substances 0.000 claims description 3
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- 239000000843 powder Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000000829 suppository Substances 0.000 claims description 3
- 206010059245 Angiopathy Diseases 0.000 claims description 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 2
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- 230000002093 peripheral effect Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 206010043540 Thromboangiitis obliterans Diseases 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
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- 229940126062 Compound A Drugs 0.000 description 17
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 17
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- 235000019441 ethanol Nutrition 0.000 description 9
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 5
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
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- 229940070851 pyridinolcarbamate Drugs 0.000 description 3
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- 239000003871 white petrolatum Substances 0.000 description 3
- 239000001043 yellow dye Substances 0.000 description 3
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- YHNOBCUFJJRVOP-UHFFFAOYSA-N 4-oxo-3h-phthalazine-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NNC(=O)C2=C1 YHNOBCUFJJRVOP-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
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- 206010020772 Hypertension Diseases 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- YEKQSSHBERGOJK-UHFFFAOYSA-N Pyricarbate Chemical compound CNC(=O)OCC1=CC=CC(COC(=O)NC)=N1 YEKQSSHBERGOJK-UHFFFAOYSA-N 0.000 description 2
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- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
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- 239000006228 supernatant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 201000005060 thrombophlebitis Diseases 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46058643A JPS5116430B2 (enrdf_load_stackoverflow) | 1971-08-05 | 1971-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2237832A1 true DE2237832A1 (de) | 1973-02-15 |
Family
ID=13090247
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2237832A Pending DE2237832A1 (de) | 1971-08-05 | 1972-08-01 | Verfahren zur herstellung von 4hydroxymethyl-1-keto-1,2-dihydrophthalazin |
| DE2238566A Pending DE2238566A1 (de) | 1971-08-05 | 1972-08-04 | Neue phthalazonderivate und verfahren zu deren herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2238566A Pending DE2238566A1 (de) | 1971-08-05 | 1972-08-04 | Neue phthalazonderivate und verfahren zu deren herstellung |
Country Status (23)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR205004A1 (es) * | 1973-10-30 | 1976-03-31 | Ishikawa M | Procedimiento para preparar derivados de 6,8-dialquil-7-alcoxi-carbonil-4-hidroximetil-1-ftalazona y la 7,8-lactona |
| NL7702763A (nl) * | 1976-03-18 | 1977-09-20 | Takio Shimamoto En Masayuki Is | Werkwijze voor de bereiding van thromboxaan- -antagonisten en van preparaten die deze stof- fen bevatten. |
| IE47592B1 (en) * | 1977-12-29 | 1984-05-02 | Ici Ltd | Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture |
| US4293553A (en) * | 1978-08-11 | 1981-10-06 | Masayuki Ishikawa | 1-Phthalazone derivatives, and use thereof |
| US4861778A (en) * | 1986-06-16 | 1989-08-29 | Research Corporation | 2,3-dihydrophthalazine-1,4-diones |
| CH683965A5 (it) * | 1993-02-19 | 1994-06-30 | Limad Marketing Exp & Imp | Composti della classe dei ftalidrazidici come sostanza attiva in agenti antinfiammatori ed antitossici. |
| DE102005011822A1 (de) * | 2005-03-15 | 2006-09-21 | Merck Patent Gmbh | Phthalazinone |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE687916A (enrdf_load_stackoverflow) * | 1965-10-12 | 1967-03-16 |
-
1971
- 1971-08-05 JP JP46058643A patent/JPS5116430B2/ja not_active Expired
-
1972
- 1972-07-21 AU AU44843/72A patent/AU461281B2/en not_active Expired
- 1972-07-24 AR AR243236A patent/AR197089A1/es active
- 1972-07-24 DK DK366572A patent/DK131857C/da not_active IP Right Cessation
- 1972-07-24 US US275171A patent/US3864343A/en not_active Expired - Lifetime
- 1972-07-24 AR AR243235A patent/AR194123A1/es active
- 1972-07-25 IE IE1047/72A patent/IE36598B1/xx unknown
- 1972-07-25 IE IE1046/72A patent/IE36597B1/xx unknown
- 1972-07-25 AU AU44940/72A patent/AU461018B2/en not_active Expired
- 1972-07-25 GB GB3482172A patent/GB1404367A/en not_active Expired
- 1972-07-25 GB GB3482072A patent/GB1404368A/en not_active Expired
- 1972-07-27 ZA ZA725202A patent/ZA725202B/xx unknown
- 1972-07-27 NL NL7210369A patent/NL7210369A/xx unknown
- 1972-07-27 NL NL727210370A patent/NL151261B/xx not_active IP Right Cessation
- 1972-07-27 ZA ZA725203A patent/ZA725203B/xx unknown
- 1972-07-28 SE SE7209886A patent/SE408177B/xx unknown
- 1972-07-31 DK DK377872A patent/DK143159C/da not_active IP Right Cessation
- 1972-08-01 DE DE2237832A patent/DE2237832A1/de active Pending
- 1972-08-02 ES ES405456A patent/ES405456A1/es not_active Expired
- 1972-08-03 SU SU7201817033A patent/SU577986A3/ru active
- 1972-08-03 BE BE787138A patent/BE787138A/xx not_active IP Right Cessation
- 1972-08-03 SE SE7210119A patent/SE406587B/xx unknown
- 1972-08-03 BE BE787139A patent/BE787139A/xx not_active IP Right Cessation
- 1972-08-03 YU YU2013/72A patent/YU35245B/xx unknown
- 1972-08-04 CA CA148,812A patent/CA966489A/en not_active Expired
- 1972-08-04 FR FR7228258A patent/FR2150736B1/fr not_active Expired
- 1972-08-04 LU LU65856A patent/LU65856A1/xx unknown
- 1972-08-04 HU HUIO186A patent/HU165815B/hu unknown
- 1972-08-04 CA CA148,813A patent/CA999236A/en not_active Expired
- 1972-08-04 HU HUIO185A patent/HU163726B/hu unknown
- 1972-08-04 FR FR7228257A patent/FR2150735B1/fr not_active Expired
- 1972-08-04 ES ES405555A patent/ES405555A1/es not_active Expired
- 1972-08-04 CH CH1160372A patent/CH580081A5/xx not_active IP Right Cessation
- 1972-08-04 CH CH1160472A patent/CH577980A5/xx not_active IP Right Cessation
- 1972-08-04 NO NO2793/72A patent/NO134113C/no unknown
- 1972-08-04 SU SU1814854A patent/SU513622A3/ru active
- 1972-08-04 AT AT852473A patent/AT320658B/de not_active IP Right Cessation
- 1972-08-04 AT AT06734/72A patent/AT317233B/de not_active IP Right Cessation
- 1972-08-04 CS CS7200005457A patent/CS180587B2/cs unknown
- 1972-08-04 CS CS7200005458A patent/CS180588B2/cs unknown
- 1972-08-04 LU LU65855A patent/LU65855A1/xx unknown
- 1972-08-04 DE DE2238566A patent/DE2238566A1/de active Pending
-
1973
- 1973-08-14 AR AR249572A patent/AR197156A1/es active
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