CH642951A5 - 4,5,6,7-tetrahydro-1h (ou 2h)-indazoles tautomeres et composition pharmaceutique les contenant. - Google Patents
4,5,6,7-tetrahydro-1h (ou 2h)-indazoles tautomeres et composition pharmaceutique les contenant. Download PDFInfo
- Publication number
- CH642951A5 CH642951A5 CH605879A CH605879A CH642951A5 CH 642951 A5 CH642951 A5 CH 642951A5 CH 605879 A CH605879 A CH 605879A CH 605879 A CH605879 A CH 605879A CH 642951 A5 CH642951 A5 CH 642951A5
- Authority
- CH
- Switzerland
- Prior art keywords
- tetrahydro
- indazole
- amino
- propyl
- formulas
- Prior art date
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- 150000004678 hydrides Chemical class 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
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- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
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- REPVNSJSTLRQEQ-UHFFFAOYSA-N n,n-dimethylacetamide;n,n-dimethylformamide Chemical compound CN(C)C=O.CN(C)C(C)=O REPVNSJSTLRQEQ-UHFFFAOYSA-N 0.000 description 1
- JOEVYUJEEWNTMZ-UHFFFAOYSA-N n-(4,5,6,7-tetrahydro-1h-indazol-5-yl)acetamide Chemical compound C1C(NC(=O)C)CCC2=NNC=C21 JOEVYUJEEWNTMZ-UHFFFAOYSA-N 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical group CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- YRTWNFXASSUQEW-UHFFFAOYSA-M sodium;methanol;acetate Chemical compound [Na+].OC.CC([O-])=O YRTWNFXASSUQEW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US506479A | 1979-01-22 | 1979-01-22 | |
| US06/020,559 US4276300A (en) | 1979-01-22 | 1979-03-15 | Amino-substituted-4,5,6,7-tetrahydro-1H (or 2H)-indazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH642951A5 true CH642951A5 (fr) | 1984-05-15 |
Family
ID=26673876
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH605879A CH642951A5 (fr) | 1979-01-22 | 1979-06-28 | 4,5,6,7-tetrahydro-1h (ou 2h)-indazoles tautomeres et composition pharmaceutique les contenant. |
| CH457383A CH646955A5 (fr) | 1979-01-22 | 1983-08-22 | 4,5,6,7-tetrahydro-1h(ou 2h)-indazol-6-ones tautomeres et leurs enol-ethers alkyliques. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH457383A CH646955A5 (fr) | 1979-01-22 | 1983-08-22 | 4,5,6,7-tetrahydro-1h(ou 2h)-indazol-6-ones tautomeres et leurs enol-ethers alkyliques. |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4276300A (OSRAM) |
| EP (1) | EP0013789B1 (OSRAM) |
| AR (1) | AR223977A1 (OSRAM) |
| AT (1) | AT364827B (OSRAM) |
| AU (1) | AU522610B2 (OSRAM) |
| BE (1) | BE877330A (OSRAM) |
| BG (5) | BG32565A3 (OSRAM) |
| CA (1) | CA1120932A (OSRAM) |
| CH (2) | CH642951A5 (OSRAM) |
| DD (4) | DD148047A5 (OSRAM) |
| DE (1) | DE2964668D1 (OSRAM) |
| DK (1) | DK149848C (OSRAM) |
| EG (1) | EG14280A (OSRAM) |
| ES (3) | ES482086A1 (OSRAM) |
| FI (1) | FI792048A7 (OSRAM) |
| FR (4) | FR2446824A1 (OSRAM) |
| GB (2) | GB2040916B (OSRAM) |
| GR (1) | GR72470B (OSRAM) |
| HU (1) | HU186710B (OSRAM) |
| IE (1) | IE48358B1 (OSRAM) |
| IL (1) | IL57666A (OSRAM) |
| LU (1) | LU81441A1 (OSRAM) |
| NZ (2) | NZ190833A (OSRAM) |
| PH (2) | PH15816A (OSRAM) |
| PL (1) | PL118618B1 (OSRAM) |
| PT (1) | PT69827A (OSRAM) |
| RO (5) | RO80296A (OSRAM) |
| ZA (1) | ZA793245B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4622398A (en) * | 1985-06-24 | 1986-11-11 | Eli Lilly And Company | Dialkylaminotetrahydroquinazoline |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6707299A (OSRAM) * | 1966-07-16 | 1968-01-17 |
-
1979
- 1979-03-15 US US06/020,559 patent/US4276300A/en not_active Expired - Lifetime
- 1979-06-26 IL IL57666A patent/IL57666A/xx unknown
- 1979-06-26 CA CA000330568A patent/CA1120932A/en not_active Expired
- 1979-06-26 DK DK268279A patent/DK149848C/da not_active IP Right Cessation
- 1979-06-26 NZ NZ190833A patent/NZ190833A/en unknown
- 1979-06-26 HU HU832080A patent/HU186710B/hu not_active IP Right Cessation
- 1979-06-26 NZ NZ199870A patent/NZ199870A/en unknown
- 1979-06-26 PT PT69827A patent/PT69827A/pt unknown
- 1979-06-27 LU LU81441A patent/LU81441A1/xx unknown
- 1979-06-27 EG EG385/79A patent/EG14280A/xx active
- 1979-06-27 PH PH22697A patent/PH15816A/en unknown
- 1979-06-27 AU AU48443/79A patent/AU522610B2/en not_active Ceased
- 1979-06-27 RO RO79102333A patent/RO80296A/ro unknown
- 1979-06-27 RO RO79102332A patent/RO80295A/ro unknown
- 1979-06-27 RO RO7997975A patent/RO77324A/ro unknown
- 1979-06-27 FR FR7916574A patent/FR2446824A1/fr active Granted
- 1979-06-27 RO RO1979102331A patent/RO80294A/ro unknown
- 1979-06-28 BG BG045170A patent/BG32565A3/xx unknown
- 1979-06-28 BG BG045171A patent/BG32566A3/xx unknown
- 1979-06-28 CH CH605879A patent/CH642951A5/fr not_active IP Right Cessation
- 1979-06-28 EP EP79301252A patent/EP0013789B1/en not_active Expired
- 1979-06-28 BG BG044132A patent/BG32564A3/xx unknown
- 1979-06-28 BG BG045173A patent/BG32568A3/xx unknown
- 1979-06-28 BE BE1/9439A patent/BE877330A/xx not_active IP Right Cessation
- 1979-06-28 GR GR59464A patent/GR72470B/el unknown
- 1979-06-28 AT AT0452679A patent/AT364827B/de not_active IP Right Cessation
- 1979-06-28 DE DE7979301252T patent/DE2964668D1/de not_active Expired
- 1979-06-28 GB GB7922531A patent/GB2040916B/en not_active Expired
- 1979-06-28 BG BG045172A patent/BG32567A3/xx unknown
- 1979-06-28 FI FI792048A patent/FI792048A7/fi not_active Application Discontinuation
- 1979-06-29 ES ES482086A patent/ES482086A1/es not_active Expired
- 1979-06-29 ZA ZA793245A patent/ZA793245B/xx unknown
- 1979-06-29 ES ES482082A patent/ES482082A1/es not_active Expired
- 1979-06-29 DD DD79217947A patent/DD148047A5/de unknown
- 1979-06-29 DD DD79217948A patent/DD148048A5/de unknown
- 1979-06-29 AR AR277114A patent/AR223977A1/es active
- 1979-06-29 DD DD79213990A patent/DD144669A5/de unknown
- 1979-06-29 ES ES482088A patent/ES482088A1/es not_active Expired
- 1979-06-29 PL PL1979216717A patent/PL118618B1/pl unknown
- 1979-06-29 DD DD79217949A patent/DD148049A5/de unknown
- 1979-08-08 IE IE1211/79A patent/IE48358B1/en unknown
- 1979-11-06 FR FR7927316A patent/FR2446827A1/fr active Granted
- 1979-11-06 FR FR7927314A patent/FR2446825A1/fr active Granted
- 1979-11-06 FR FR7927315A patent/FR2446826A1/fr active Granted
-
1980
- 1980-01-21 PH PH23527A patent/PH15880A/en unknown
- 1980-06-27 RO RO80102334A patent/RO80297A/ro unknown
-
1983
- 1983-03-30 GB GB08308859A patent/GB2118547B/en not_active Expired
- 1983-08-22 CH CH457383A patent/CH646955A5/fr not_active IP Right Cessation
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