DD144666A5 - Verfahren zur herstellung von tetrahydro-2h-benzo eckige klammer auf c eckige klammer zu pyrrolen - Google Patents
Verfahren zur herstellung von tetrahydro-2h-benzo eckige klammer auf c eckige klammer zu pyrrolen Download PDFInfo
- Publication number
- DD144666A5 DD144666A5 DD79213988A DD21398879A DD144666A5 DD 144666 A5 DD144666 A5 DD 144666A5 DD 79213988 A DD79213988 A DD 79213988A DD 21398879 A DD21398879 A DD 21398879A DD 144666 A5 DD144666 A5 DD 144666A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- benzo
- tetrahydro
- pyrrole
- formula
- compounds
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 41
- -1 pyrrole compound Chemical class 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 13
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- 239000002253 acid Substances 0.000 claims description 9
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- 150000001350 alkyl halides Chemical class 0.000 claims description 6
- 229910052987 metal hydride Inorganic materials 0.000 claims description 6
- 150000004681 metal hydrides Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 5
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 239000011780 sodium chloride Substances 0.000 description 4
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- 239000000284 extract Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
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- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
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- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical class CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000011976 maleic acid 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
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 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
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- JPCUUMJCCCQVFF-UHFFFAOYSA-N n-[3-(dimethylaminomethylidene)-4-oxocyclohexyl]acetamide Chemical compound CN(C)C=C1CC(NC(C)=O)CCC1=O JPCUUMJCCCQVFF-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
- 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
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical class CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 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
- 238000011176 pooling Methods 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- GZWNUORNEQHOAW-UHFFFAOYSA-M potassium;2-aminoacetate Chemical compound [K+].NCC([O-])=O GZWNUORNEQHOAW-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical class CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction 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
- 230000007017 scission Effects 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US506379A | 1979-01-22 | 1979-01-22 | |
| US06/020,560 US4235776A (en) | 1979-03-15 | 1979-03-15 | Tetrahydro-2H-benzo[c]pyrroles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD144666A5 true DD144666A5 (de) | 1980-10-29 |
Family
ID=26673874
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79213988A DD144666A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von tetrahydro-2h-benzo eckige klammer auf c eckige klammer zu pyrrolen |
| DD79220466A DD150745A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von tetrahydro-2h-benzo[c]pyrrolen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79220466A DD150745A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von tetrahydro-2h-benzo[c]pyrrolen |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP0014792B1 (en, 2012) |
| AR (1) | AR227134A1 (en, 2012) |
| AT (1) | AT360516B (en, 2012) |
| AU (1) | AU525367B2 (en, 2012) |
| BE (1) | BE877329A (en, 2012) |
| BG (2) | BG34761A3 (en, 2012) |
| CA (1) | CA1105473A (en, 2012) |
| CH (2) | CH643244A5 (en, 2012) |
| DD (2) | DD144666A5 (en, 2012) |
| DE (1) | DE2964139D1 (en, 2012) |
| DK (1) | DK155600C (en, 2012) |
| EG (1) | EG14069A (en, 2012) |
| ES (2) | ES482083A1 (en, 2012) |
| FI (1) | FI792045A7 (en, 2012) |
| FR (2) | FR2446817A1 (en, 2012) |
| GB (2) | GB2040914B (en, 2012) |
| GR (1) | GR72398B (en, 2012) |
| IE (1) | IE48648B1 (en, 2012) |
| IL (1) | IL57664A (en, 2012) |
| LU (1) | LU81438A1 (en, 2012) |
| NZ (1) | NZ190831A (en, 2012) |
| PH (1) | PH18288A (en, 2012) |
| PL (1) | PL122798B1 (en, 2012) |
| PT (1) | PT69826A (en, 2012) |
| RO (1) | RO77806A (en, 2012) |
| ZA (1) | ZA793242B (en, 2012) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1019111A (en) * | 1962-12-04 | 1966-02-02 | Arnzneimittelwerk Dresden Veb | Salts of 5-amino-isoindoline |
| BE634851A (en, 2012) * | 1963-05-15 | 1900-01-01 | ||
| FR3396M (fr) * | 1963-07-30 | 1965-06-28 | Dresden Arzneimittel | Dérivés n-acylés de la 5-amino-isoindoline et de leurs sels. |
-
1979
- 1979-06-26 IL IL57664A patent/IL57664A/xx unknown
- 1979-06-26 NZ NZ190831A patent/NZ190831A/en unknown
- 1979-06-26 CA CA330,566A patent/CA1105473A/en not_active Expired
- 1979-06-26 DK DK268179A patent/DK155600C/da not_active IP Right Cessation
- 1979-06-26 PT PT69826A patent/PT69826A/pt unknown
- 1979-06-27 LU LU81438A patent/LU81438A1/xx unknown
- 1979-06-27 AU AU48442/79A patent/AU525367B2/en not_active Ceased
- 1979-06-27 EG EG383/79A patent/EG14069A/xx active
- 1979-06-27 RO RO7997974A patent/RO77806A/ro unknown
- 1979-06-27 FR FR7916573A patent/FR2446817A1/fr active Granted
- 1979-06-27 PH PH22696A patent/PH18288A/en unknown
- 1979-06-28 AT AT452779A patent/AT360516B/de not_active IP Right Cessation
- 1979-06-28 GB GB7922528A patent/GB2040914B/en not_active Expired
- 1979-06-28 FI FI792045A patent/FI792045A7/fi not_active Application Discontinuation
- 1979-06-28 GR GR59463A patent/GR72398B/el unknown
- 1979-06-28 EP EP79301248A patent/EP0014792B1/en not_active Expired
- 1979-06-28 CH CH605779A patent/CH643244A5/fr not_active IP Right Cessation
- 1979-06-28 BG BG044129A patent/BG34761A3/xx unknown
- 1979-06-28 DE DE7979301248T patent/DE2964139D1/de not_active Expired
- 1979-06-28 BG BG045095A patent/BG34762A3/xx unknown
- 1979-06-28 BE BE1/9438A patent/BE877329A/xx not_active IP Right Cessation
- 1979-06-29 AR AR277115A patent/AR227134A1/es active
- 1979-06-29 PL PL1979216718A patent/PL122798B1/pl unknown
- 1979-06-29 DD DD79213988A patent/DD144666A5/de unknown
- 1979-06-29 DD DD79220466A patent/DD150745A5/de unknown
- 1979-06-29 ZA ZA793242A patent/ZA793242B/xx unknown
- 1979-06-29 ES ES482083A patent/ES482083A1/es not_active Expired
- 1979-08-08 IE IE1208/79A patent/IE48648B1/en unknown
- 1979-11-06 FR FR7927313A patent/FR2446818A1/fr active Granted
-
1980
- 1980-03-28 ES ES490079A patent/ES8104224A1/es not_active Expired
-
1982
- 1982-05-07 GB GB08213212A patent/GB2121029B/en not_active Expired
-
1983
- 1983-06-27 CH CH351683A patent/CH644595A5/fr not_active IP Right Cessation
Also Published As
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