DE1670643B2 - 2-guanidomethyl-perhydroazocin, verfahren zu dessen herstellung und 2-guanidinomethyl-perhydroazocin enthaltende pharmazeutische praeparate - Google Patents
2-guanidomethyl-perhydroazocin, verfahren zu dessen herstellung und 2-guanidinomethyl-perhydroazocin enthaltende pharmazeutische praeparateInfo
- Publication number
- DE1670643B2 DE1670643B2 DE1967E0035391 DEE0035391A DE1670643B2 DE 1670643 B2 DE1670643 B2 DE 1670643B2 DE 1967E0035391 DE1967E0035391 DE 1967E0035391 DE E0035391 A DEE0035391 A DE E0035391A DE 1670643 B2 DE1670643 B2 DE 1670643B2
- Authority
- DE
- Germany
- Prior art keywords
- perhydroazocine
- guanidinomethyl
- sulfate
- perhydroazocin
- guanidomethyl
- 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
- 238000000034 method Methods 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 3
- ZCVAIGPGEINFCX-UHFFFAOYSA-N guanazodine Chemical compound NC(=N)NCC1CCCCCCN1 ZCVAIGPGEINFCX-UHFFFAOYSA-N 0.000 title description 2
- 239000000047 product Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- -1 perhydroazocin sulfate Chemical compound 0.000 description 10
- 230000000694 effects Effects 0.000 description 7
- 230000036772 blood pressure Effects 0.000 description 6
- ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 6
- 229960003602 guanethidine Drugs 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 206010015995 Eyelid ptosis Diseases 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 201000003004 ptosis Diseases 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- CTRTUKIIAAAKIJ-UHFFFAOYSA-N (c-azaniumylcarbonimidoyl)-propylazanium;sulfate Chemical compound OS(O)(=O)=O.CCCN=C(N)N CTRTUKIIAAAKIJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000001800 adrenalinergic effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 2
- 230000003066 neuroblocking effect Effects 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002889 sympathetic effect Effects 0.000 description 2
- 230000035488 systolic blood pressure Effects 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- WTLKTXIHIHFSGU-UHFFFAOYSA-N 2-nitrosoguanidine Chemical compound NC(N)=NN=O WTLKTXIHIHFSGU-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000520330 Otomys irroratus Species 0.000 description 1
- 241000030360 Peromyscus truei Species 0.000 description 1
- 241000144290 Sigmodon hispidus Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZZTURJAZCMUWEP-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen sulfate Chemical compound NC(N)=N.OS(O)(=O)=O ZZTURJAZCMUWEP-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- YUFWAVFNITUSHI-UHFFFAOYSA-N guanethidine monosulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.NC(=N)NCCN1CCCCCCC1 YUFWAVFNITUSHI-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000002988 nephrogenic effect Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000826 nictitating membrane Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D227/00—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00
- C07D227/02—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D227/04—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE001327 | 1966-12-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1670643A1 DE1670643A1 (de) | 1971-03-18 |
| DE1670643B2 true DE1670643B2 (de) | 1977-06-30 |
Family
ID=10995214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967E0035391 Granted DE1670643B2 (de) | 1966-12-30 | 1967-12-14 | 2-guanidomethyl-perhydroazocin, verfahren zu dessen herstellung und 2-guanidinomethyl-perhydroazocin enthaltende pharmazeutische praeparate |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT277279B (cs) |
| BE (1) | BE708792A (cs) |
| CH (1) | CH490384A (cs) |
| CS (1) | CS150210B2 (cs) |
| DE (1) | DE1670643B2 (cs) |
| DK (1) | DK115262B (cs) |
| FR (1) | FR6962M (cs) |
| GB (1) | GB1216096A (cs) |
| IL (1) | IL29154A (cs) |
| NL (1) | NL6717792A (cs) |
| PL (1) | PL69793B1 (cs) |
| SE (1) | SE322520B (cs) |
| YU (1) | YU32284B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6847729B1 (en) | 1999-04-21 | 2005-01-25 | Fairfield Imaging Limited | Microscopy |
-
1967
- 1967-12-14 DE DE1967E0035391 patent/DE1670643B2/de active Granted
- 1967-12-15 CH CH1758567A patent/CH490384A/de not_active IP Right Cessation
- 1967-12-15 AT AT1131667A patent/AT277279B/de active
- 1967-12-15 GB GB57195/67A patent/GB1216096A/en not_active Expired
- 1967-12-18 IL IL2915467A patent/IL29154A/xx unknown
- 1967-12-21 YU YU250467A patent/YU32284B/xx unknown
- 1967-12-22 DK DK650467A patent/DK115262B/da not_active IP Right Cessation
- 1967-12-27 PL PL12435067A patent/PL69793B1/pl unknown
- 1967-12-28 FR FR133988A patent/FR6962M/fr not_active Expired
- 1967-12-29 NL NL6717792A patent/NL6717792A/xx unknown
- 1967-12-29 SE SE1810367A patent/SE322520B/xx unknown
- 1967-12-29 BE BE708792D patent/BE708792A/xx not_active IP Right Cessation
- 1967-12-29 CS CS928967A patent/CS150210B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE322520B (cs) | 1970-04-13 |
| CS150210B2 (cs) | 1973-09-04 |
| GB1216096A (en) | 1970-12-16 |
| NL6717792A (cs) | 1968-07-01 |
| YU250467A (en) | 1974-02-28 |
| IL29154A (en) | 1971-10-20 |
| DE1670643A1 (de) | 1971-03-18 |
| AT277279B (de) | 1969-12-29 |
| FR6962M (cs) | 1969-05-19 |
| CH490384A (de) | 1970-05-15 |
| PL69793B1 (cs) | 1973-10-31 |
| BE708792A (cs) | 1968-05-02 |
| DK115262B (da) | 1969-09-22 |
| YU32284B (en) | 1974-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |