NO131986B - - Google Patents
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- Publication number
- NO131986B NO131986B NO1058/71A NO105871A NO131986B NO 131986 B NO131986 B NO 131986B NO 1058/71 A NO1058/71 A NO 1058/71A NO 105871 A NO105871 A NO 105871A NO 131986 B NO131986 B NO 131986B
- Authority
- NO
- Norway
- Prior art keywords
- mol
- ester
- general formula
- azidobenzaldehyde
- azidophenyl
- Prior art date
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- -1 acyl fatty acid esters Chemical class 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- UCJDGRYGBYCWMS-UHFFFAOYSA-N 3-azidobenzaldehyde Chemical compound [N-]=[N+]=NC1=CC=CC(C=O)=C1 UCJDGRYGBYCWMS-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 7
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 7
- NHTBGGLIHGSCFA-UHFFFAOYSA-N 2-azidobenzaldehyde Chemical class [N-]=[N+]=NC1=CC=CC=C1C=O NHTBGGLIHGSCFA-UHFFFAOYSA-N 0.000 description 5
- SDJOUGYEUFYPLL-UHFFFAOYSA-N 4-azidobenzaldehyde Chemical compound [N-]=[N+]=NC1=CC=C(C=O)C=C1 SDJOUGYEUFYPLL-UHFFFAOYSA-N 0.000 description 5
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 description 4
- BDCLDNALSPBWPQ-UHFFFAOYSA-N 3-oxohexanoic acid Chemical compound CCCC(=O)CC(O)=O BDCLDNALSPBWPQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000004531 blood pressure lowering effect Effects 0.000 description 2
- 230000003788 cerebral perfusion Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- BBBJXPCSKOPGLI-UHFFFAOYSA-N 2-propoxyethyl 3-oxobutanoate Chemical compound CCCOCCOC(=O)CC(C)=O BBBJXPCSKOPGLI-UHFFFAOYSA-N 0.000 description 1
- REIYHFWZISXFKU-UHFFFAOYSA-N Butyl acetoacetate Chemical compound CCCCOC(=O)CC(C)=O REIYHFWZISXFKU-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000003440 anti-fibrillation Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 210000003748 coronary sinus Anatomy 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IVJSIASDHCFCQI-UHFFFAOYSA-N diethyl 4-(3-azidophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC(N=[N+]=[N-])=C1 IVJSIASDHCFCQI-UHFFFAOYSA-N 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- NMZBLCYLRMWDMF-UHFFFAOYSA-N dimethyl 4-(3-azidophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC(N=[N+]=[N-])=C1 NMZBLCYLRMWDMF-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 1
- UDRCONFHWYGWFI-UHFFFAOYSA-N ethyl 3-oxopentanoate Chemical compound CCOC(=O)CC(=O)CC UDRCONFHWYGWFI-UHFFFAOYSA-N 0.000 description 1
- XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000003235 vasospasmolytic effect Effects 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
- C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
- C07D211/84—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 two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2013431A DE2013431C3 (de) | 1970-03-20 | 1970-03-20 | 4-Azidophenyl-l,4-dihydropyridin-3,5-dicarbonsäureester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131986B true NO131986B (en, 2012) | 1975-05-26 |
| NO131986C NO131986C (en, 2012) | 1975-09-03 |
Family
ID=5765765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1058/71A NO131986C (en, 2012) | 1970-03-20 | 1971-03-18 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US3708489A (en, 2012) |
| JP (1) | JPS5521032B1 (en, 2012) |
| AT (1) | AT303040B (en, 2012) |
| BE (1) | BE764556A (en, 2012) |
| CH (1) | CH559179A5 (en, 2012) |
| CS (2) | CS160140B2 (en, 2012) |
| DE (1) | DE2013431C3 (en, 2012) |
| FI (1) | FI54295C (en, 2012) |
| FR (1) | FR2085727B1 (en, 2012) |
| GB (1) | GB1305795A (en, 2012) |
| IE (1) | IE35233B1 (en, 2012) |
| IL (1) | IL36320A (en, 2012) |
| NL (1) | NL169468C (en, 2012) |
| NO (1) | NO131986C (en, 2012) |
| SE (1) | SE364710B (en, 2012) |
| ZA (1) | ZA711597B (en, 2012) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2005116C3 (de) * | 1970-02-05 | 1980-02-14 | Bayer Ag, 5090 Leverkusen | Symmetrische 1,4-Dihydropyridin-3,5-dicarbonsäureester |
| US4021434A (en) * | 1972-01-22 | 1977-05-03 | Yamanouchi Pharmaceutical Co., Ltd. | Sodium β-[2,6-dimethyl-3,5-bis(ethoxycarbonyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-1-yl]ethyl sulfate |
| GB1430961A (en) * | 1972-01-22 | 1976-04-07 | Yamanouchi Pharma Co Ltd | 1-substituted-1,4-dihyddrypyridine derivatives |
| US3992545A (en) * | 1972-03-06 | 1976-11-16 | Bayer Aktiengesellschaft | 2-Amino-4,5-dihydropyridine derivatives in pharmaceutical compositions |
| DE2210674C3 (de) * | 1972-03-06 | 1981-09-24 | Bayer Ag, 5090 Leverkusen | 2-Amino-6-methyl-1,4-dihydropyridine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
| US3857849A (en) * | 1973-02-28 | 1974-12-31 | Bayer Ag | 2-amino-1,4-dihydropyridine derivatives |
| DE2210672C3 (de) * | 1972-03-06 | 1980-03-20 | Bayer Ag, 5090 Leverkusen | N-substituierte unsymmetrische 1 ^-Dihydropyridin-S^-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| US3985886A (en) * | 1972-03-06 | 1976-10-12 | Bayer Aktiengesellschaft | 2-Amino-4,5-dihydropyridine derivatives and process for their preparation |
| US3939171A (en) * | 1972-03-06 | 1976-02-17 | Bayer Aktiengesellschaft | 2-Amino-1,4-dihydropyridine derivatives |
| DD106832A5 (en, 2012) * | 1972-03-06 | 1974-07-05 | ||
| US3957998A (en) * | 1972-03-06 | 1976-05-18 | Bayer Aktiengesellschaft | Use of 2,6-diamino-4-substituted-1,4-dihydropyridine-3,5-dicarboxylic acid esters for effecting coronary vessel dilation and treating hypertension |
| US3887558A (en) * | 1972-03-06 | 1975-06-03 | Bayer Ag | Process for producing 2,6-diamino -1,4- dihydro-3,5-pyridine-dicarboxylates and derivatives thereof |
| US3917620A (en) * | 1972-03-06 | 1975-11-04 | Bayer Ag | 2-Amino-4,5-dihydropyridine derivatives |
| US3996234A (en) * | 1972-04-18 | 1976-12-07 | Bayer Aktiengesellschaft | 1,4-Dihydropyridine carboxylic acid esters |
| US3974275A (en) * | 1972-04-18 | 1976-08-10 | Bayer Aktiengesellschaft | 1,4-Dihydropyridine carboxylic acid esters useful as coronary vessel dilators and anti-hypertensives |
| US4136187A (en) * | 1972-08-12 | 1979-01-23 | Bayer Aktiengesellschaft | Antihypertensive 2-amino-4,5-dihydropyridine derivatives |
| DE2239815C2 (de) * | 1972-08-12 | 1983-02-10 | Bayer Ag, 5090 Leverkusen | 2-Alkylamino-dihydropyridine, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel |
| DE2242787C2 (de) * | 1972-08-31 | 1982-01-21 | Bayer Ag, 5090 Leverkusen | 4-Phenyl-6-amino-3,4-dihydropyridon-(2)-3,5-dicarbonsäure-diäthylesterderivate, ein Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| US4002762A (en) * | 1973-03-03 | 1977-01-11 | Bayer Aktiengesellschaft | 2-Amino-3,4-dihydropyridines used to effect coronary vessel dilation and treat hypertension |
| US4020178A (en) * | 1973-07-12 | 1977-04-26 | Bayer Aktiengesellschaft | 1,4-Dihydropyridine esters used as coronary dilators and anti-hypertensives |
| NO883326L (no) * | 1987-08-11 | 1989-02-13 | Bayer Ag | Dhp-retard-tilberedning. |
| US5216172A (en) * | 1988-02-24 | 1993-06-01 | Ajinomoto Co., Inc. | 1,4-dihydropyridine-4-aryl-2,6-dimethyl-3,5-dicarboxylates useful as agents against drug resistant tumor cells |
| EP0330470A3 (en) * | 1988-02-24 | 1992-01-02 | Ajinomoto Co., Inc. | 1,4-dihydropyridine derivatives useful against tumour cells |
-
1970
- 1970-03-20 DE DE2013431A patent/DE2013431C3/de not_active Expired
-
1971
- 1971-03-02 IL IL36320A patent/IL36320A/en unknown
- 1971-03-09 IE IE293/71A patent/IE35233B1/xx unknown
- 1971-03-10 FI FI694/71A patent/FI54295C/fi active
- 1971-03-11 ZA ZA711597A patent/ZA711597B/xx unknown
- 1971-03-11 CS CS3638*A patent/CS160140B2/cs unknown
- 1971-03-11 CS CS1794A patent/CS160139B2/cs unknown
- 1971-03-12 SE SE03213/71A patent/SE364710B/xx unknown
- 1971-03-17 US US00125427A patent/US3708489A/en not_active Expired - Lifetime
- 1971-03-18 NL NLAANVRAGE7103672,A patent/NL169468C/xx not_active IP Right Cessation
- 1971-03-18 NO NO1058/71A patent/NO131986C/no unknown
- 1971-03-19 FR FR7109866A patent/FR2085727B1/fr not_active Expired
- 1971-03-19 CH CH405371A patent/CH559179A5/xx not_active IP Right Cessation
- 1971-03-19 BE BE764556A patent/BE764556A/xx not_active IP Right Cessation
- 1971-03-19 AT AT239271A patent/AT303040B/de not_active IP Right Cessation
- 1971-03-19 JP JP1545571A patent/JPS5521032B1/ja active Pending
- 1971-04-19 GB GB2454071*A patent/GB1305795A/en not_active Expired
-
1972
- 1972-06-02 US US00259289A patent/US3773956A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5521032B1 (en, 2012) | 1980-06-06 |
| NL169468B (nl) | 1982-02-16 |
| FR2085727B1 (en, 2012) | 1974-09-27 |
| IE35233B1 (en) | 1975-12-24 |
| CS160140B2 (en, 2012) | 1975-02-28 |
| IL36320A0 (en) | 1971-05-26 |
| CH559179A5 (en, 2012) | 1975-02-28 |
| AT303040B (de) | 1972-11-10 |
| FI54295C (fi) | 1978-11-10 |
| DE2013431C3 (de) | 1979-12-20 |
| NO131986C (en, 2012) | 1975-09-03 |
| DE2013431B2 (de) | 1979-04-26 |
| US3708489A (en) | 1973-01-02 |
| GB1305795A (en, 2012) | 1973-02-07 |
| FI54295B (fi) | 1978-07-31 |
| NL169468C (nl) | 1982-07-16 |
| FR2085727A1 (en, 2012) | 1971-12-31 |
| IL36320A (en) | 1974-10-22 |
| ZA711597B (en) | 1972-06-28 |
| SE364710B (en, 2012) | 1974-03-04 |
| IE35233L (en) | 1971-09-20 |
| US3773956A (en) | 1973-11-20 |
| DE2013431A1 (de) | 1971-10-07 |
| SU365069A3 (en, 2012) | 1972-12-28 |
| BE764556A (fr) | 1971-09-20 |
| NL7103672A (en, 2012) | 1971-09-22 |
| CS160139B2 (en, 2012) | 1975-02-28 |
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