CH635106A5 - Dimeric indolodihydroindoles, processes for their preparation, and their use - Google Patents
Dimeric indolodihydroindoles, processes for their preparation, and their use Download PDFInfo
- Publication number
- CH635106A5 CH635106A5 CH53578A CH53578A CH635106A5 CH 635106 A5 CH635106 A5 CH 635106A5 CH 53578 A CH53578 A CH 53578A CH 53578 A CH53578 A CH 53578A CH 635106 A5 CH635106 A5 CH 635106A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- dimeric
- deoxy
- group
- chs
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
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- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical class CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- KDQAABAKXDWYSZ-SDCRJXSCSA-N leurosidine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 KDQAABAKXDWYSZ-SDCRJXSCSA-N 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical class COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- UJQMLHKSZKBMMO-UHFFFAOYSA-N n,n-diethylethanamine;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)CC UJQMLHKSZKBMMO-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class 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 class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class 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
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 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
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical class CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 150000003892 tartrate salts Chemical class 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- 229950003670 vinrosidine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76059577A | 1977-01-19 | 1977-01-19 | |
| US05/853,979 US4143041A (en) | 1977-01-19 | 1977-11-25 | 4'-Deoxyvincristine and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH635106A5 true CH635106A5 (en) | 1983-03-15 |
Family
ID=27116837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH53578A CH635106A5 (en) | 1977-01-19 | 1978-01-18 | Dimeric indolodihydroindoles, processes for their preparation, and their use |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5390299A (is") |
| AR (1) | AR217459A1 (is") |
| AT (1) | AT363620B (is") |
| BG (2) | BG33293A3 (is") |
| CA (2) | CA1088526A (is") |
| CH (1) | CH635106A5 (is") |
| CS (2) | CS194832B2 (is") |
| DD (1) | DD134527A5 (is") |
| DE (1) | DE2801748A1 (is") |
| DK (1) | DK144420C (is") |
| FR (1) | FR2378032A1 (is") |
| GB (1) | GB1593231A (is") |
| GR (1) | GR68940B (is") |
| IE (1) | IE46308B1 (is") |
| IL (1) | IL53813A (is") |
| IT (1) | IT1174356B (is") |
| MX (1) | MX5112E (is") |
| NL (1) | NL7800667A (is") |
| NZ (1) | NZ186232A (is") |
| PL (1) | PL109695B1 (is") |
| PT (1) | PT67535B (is") |
| RO (2) | RO73126A (is") |
| SE (2) | SE425852B (is") |
| YU (1) | YU7278A (is") |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0649314U (ja) * | 1992-12-11 | 1994-07-05 | ヒノマル株式会社 | 食品包装容器 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2296418B1 (is") * | 1974-12-30 | 1978-07-21 | Anvar | |
| IL48685A (en) * | 1975-01-09 | 1980-03-31 | Lilly Co Eli | Amides of vincadioline and vinblastine |
-
1978
- 1978-01-16 CS CS78292A patent/CS194832B2/cs unknown
- 1978-01-16 YU YU00072/78A patent/YU7278A/xx unknown
- 1978-01-16 PT PT67535A patent/PT67535B/pt unknown
- 1978-01-16 NZ NZ186232A patent/NZ186232A/xx unknown
- 1978-01-16 DE DE19782801748 patent/DE2801748A1/de not_active Withdrawn
- 1978-01-16 BG BG040832A patent/BG33293A3/xx unknown
- 1978-01-16 IL IL53813A patent/IL53813A/xx unknown
- 1978-01-16 GR GR55178A patent/GR68940B/el unknown
- 1978-01-16 GB GB1692/78A patent/GB1593231A/en not_active Expired
- 1978-01-16 CS CS785375A patent/CS194850B2/cs unknown
- 1978-01-16 BG BG038402A patent/BG33158A3/xx unknown
- 1978-01-17 FR FR7801262A patent/FR2378032A1/fr active Granted
- 1978-01-17 DK DK22478A patent/DK144420C/da not_active IP Right Cessation
- 1978-01-17 AR AR270733A patent/AR217459A1/es active
- 1978-01-17 CA CA295,086A patent/CA1088526A/en not_active Expired
- 1978-01-17 SE SE7800555A patent/SE425852B/sv not_active IP Right Cessation
- 1978-01-17 CA CA295,114A patent/CA1088527A/en not_active Expired
- 1978-01-18 IE IE106/78A patent/IE46308B1/en unknown
- 1978-01-18 IT IT19388/78A patent/IT1174356B/it active
- 1978-01-18 AT AT0035478A patent/AT363620B/de not_active IP Right Cessation
- 1978-01-18 CH CH53578A patent/CH635106A5/de not_active IP Right Cessation
- 1978-01-18 MX MX786780U patent/MX5112E/es unknown
- 1978-01-19 JP JP479378A patent/JPS5390299A/ja active Granted
- 1978-01-19 RO RO7892948A patent/RO73126A/ro unknown
- 1978-01-19 PL PL1978204091A patent/PL109695B1/pl unknown
- 1978-01-19 RO RO7899202A patent/RO78290A/ro unknown
- 1978-01-19 DD DD78203301A patent/DD134527A5/xx unknown
- 1978-01-19 NL NL7800667A patent/NL7800667A/xx not_active Application Discontinuation
-
1982
- 1982-07-08 SE SE8204238A patent/SE444684B/sv not_active IP Right Cessation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |