DE2328061A1 - Neue acetamidinderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate - Google Patents
Neue acetamidinderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparateInfo
- Publication number
- DE2328061A1 DE2328061A1 DE2328061A DE2328061A DE2328061A1 DE 2328061 A1 DE2328061 A1 DE 2328061A1 DE 2328061 A DE2328061 A DE 2328061A DE 2328061 A DE2328061 A DE 2328061A DE 2328061 A1 DE2328061 A1 DE 2328061A1
- Authority
- DE
- Germany
- Prior art keywords
- acetamidine
- aza
- acid addition
- salt
- mono
- 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
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- 230000008569 process Effects 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 19
- -1 3-n-propyl Chemical group 0.000 claims description 17
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical class CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
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- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
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- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 8
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- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 1
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- 235000004279 alanine Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
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- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
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- 208000022531 anorexia Diseases 0.000 description 1
- 230000001466 anti-adreneric effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
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- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
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- 229960004486 desoxycorticosterone acetate Drugs 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
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- YZMWERQXXYGACI-UHFFFAOYSA-N ethanimidamide;dihydrochloride Chemical compound Cl.Cl.CC(N)=N YZMWERQXXYGACI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
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- 210000003041 ligament Anatomy 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VQVVOFMOUZTBNC-UHFFFAOYSA-J magnesium octadecanoate oxosilicon(2+) Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)[O-].[Mg+2].[Si+2]=O.C(CCCCCCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCCCCCC)(=O)[O-] VQVVOFMOUZTBNC-UHFFFAOYSA-J 0.000 description 1
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- 229910052760 oxygen Inorganic materials 0.000 description 1
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 238000009519 pharmacological trial Methods 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2569772A GB1382602A (en) | 1972-06-01 | 1972-06-01 | Benzodioxan compounds and process for preparing the same |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2328061A1 true DE2328061A1 (de) | 1973-12-13 |
Family
ID=10231839
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2328061A Pending DE2328061A1 (de) | 1972-06-01 | 1973-06-01 | Neue acetamidinderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate |
Country Status (24)
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4806663A (en) * | 1987-04-06 | 1989-02-21 | The University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
US4851554A (en) * | 1987-04-06 | 1989-07-25 | University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
US4831156A (en) * | 1987-09-30 | 1989-05-16 | The University Of Tennessee Research Corp. | 3-substituted 2-alkyl indole derivatives |
US5427068A (en) * | 1992-09-04 | 1995-06-27 | Spread Spectrum | Rotary compressor and engine machine system |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1315372A (fr) * | 1962-02-14 | 1963-01-18 | Lakeside Lab | Nouveaux dérivés de benzodioxanne et leur préparation |
US3185692A (en) * | 1962-06-28 | 1965-05-25 | Colgate Palmolive Co | Aminoalkyl-n-benzodioxyl carbamates |
GB1038333A (en) * | 1963-02-13 | 1966-08-10 | Ici Ltd | Pharmaceutical compositions |
US3496183A (en) * | 1964-11-19 | 1970-02-17 | Egyt Gyogyszervegyeszeti Gyar | Beta-guanidino-ethyl-piperazine derivatives |
BE791501A (fr) * | 1971-11-19 | 1973-05-17 | Albert Ag Chem Werke | Diamines cycliques n,n'-disubstituees et leur procede de preparation |
-
1972
- 1972-06-01 GB GB2569772A patent/GB1382602A/en not_active Expired
-
1973
- 1973-04-04 YU YU904/73A patent/YU35020B/xx unknown
- 1973-04-23 AR AR247653A patent/AR197137A1/es active
- 1973-04-27 IE IE671/73A patent/IE37579B1/xx unknown
- 1973-04-30 ZA ZA732909A patent/ZA732909B/xx unknown
- 1973-05-08 CH CH652373A patent/CH572052A5/xx not_active IP Right Cessation
- 1973-05-11 SE SE7306694A patent/SE396078B/xx unknown
- 1973-05-14 US US360142A patent/US3891648A/en not_active Expired - Lifetime
- 1973-05-18 BE BE131261A patent/BE799718A/xx unknown
- 1973-05-22 NL NL7307108A patent/NL7307108A/xx not_active Application Discontinuation
- 1973-05-23 JP JP48058502A patent/JPS4942682A/ja active Pending
- 1973-05-25 FR FR7319050A patent/FR2186254B1/fr not_active Expired
- 1973-05-28 FI FI1712/73A patent/FI55339C/fi active
- 1973-05-28 ES ES415267A patent/ES415267A1/es not_active Expired
- 1973-05-28 AU AU56194/73A patent/AU468544B2/en not_active Expired
- 1973-05-29 IN IN1253/CAL/73A patent/IN139164B/en unknown
- 1973-05-30 OA OA54925A patent/OA04416A/xx unknown
- 1973-05-30 DK DK302373AA patent/DK142173B/da not_active IP Right Cessation
- 1973-05-30 NO NO2275/73A patent/NO137693C/no unknown
- 1973-05-31 CA CA172,904A patent/CA1003834A/en not_active Expired
- 1973-05-31 HU HULA825A patent/HU165378B/hu unknown
- 1973-05-31 SU SU1931801A patent/SU468413A3/ru active
- 1973-06-01 AT AT481573A patent/AT325042B/de not_active IP Right Cessation
- 1973-06-01 DE DE2328061A patent/DE2328061A1/de active Pending
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