DE3537715C2 - - Google Patents
Info
- Publication number
- DE3537715C2 DE3537715C2 DE3537715A DE3537715A DE3537715C2 DE 3537715 C2 DE3537715 C2 DE 3537715C2 DE 3537715 A DE3537715 A DE 3537715A DE 3537715 A DE3537715 A DE 3537715A DE 3537715 C2 DE3537715 C2 DE 3537715C2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- pyridine
- dioxino
- trimethyl
- cyano
- 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.)
- Expired - Lifetime
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 36
- -1 methoxyphenethyl Chemical group 0.000 claims description 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 10
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 8
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 208000025865 Ulcer Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 231100000397 ulcer Toxicity 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229960001722 verapamil Drugs 0.000 description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229960001340 histamine Drugs 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229960002748 norepinephrine Drugs 0.000 description 3
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 2
- 229960000620 ranitidine Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- 229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 description 1
- 102000005862 Angiotensin II Human genes 0.000 description 1
- 101800000733 Angiotensin-2 Proteins 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- 206010047163 Vasospasm Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229950006323 angiotensin ii Drugs 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical group Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848426738A GB8426738D0 (en) | 1984-10-23 | 1984-10-23 | Pyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3537715A1 DE3537715A1 (de) | 1986-04-24 |
| DE3537715C2 true DE3537715C2 (en:Method) | 1992-04-09 |
Family
ID=10568592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853537715 Granted DE3537715A1 (de) | 1984-10-23 | 1985-10-23 | Pyridinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4610990A (en:Method) |
| JP (1) | JPS61106578A (en:Method) |
| AR (1) | AR240942A1 (en:Method) |
| AT (1) | AT393682B (en:Method) |
| BE (1) | BE903403A (en:Method) |
| CA (1) | CA1286300C (en:Method) |
| CH (1) | CH665842A5 (en:Method) |
| DE (1) | DE3537715A1 (en:Method) |
| DK (1) | DK159319C (en:Method) |
| DZ (1) | DZ851A1 (en:Method) |
| ES (1) | ES8609329A1 (en:Method) |
| FI (1) | FI82249C (en:Method) |
| FR (2) | FR2571965B1 (en:Method) |
| GB (2) | GB8426738D0 (en:Method) |
| HK (1) | HK44388A (en:Method) |
| IE (1) | IE58499B1 (en:Method) |
| IT (1) | IT1190409B (en:Method) |
| LU (1) | LU86117A1 (en:Method) |
| MA (1) | MA20559A1 (en:Method) |
| MY (1) | MY102281A (en:Method) |
| NL (1) | NL8502788A (en:Method) |
| NO (1) | NO163777C (en:Method) |
| OA (1) | OA08125A (en:Method) |
| PT (1) | PT81351B (en:Method) |
| SE (1) | SE460904B (en:Method) |
| ZA (1) | ZA857650B (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3642331A1 (de) * | 1986-12-11 | 1988-06-23 | Basf Ag | Basisch substituierte phenylacetonitrile, ihre herstellung und diese enthaltende arzneimittel |
| JPH02102810U (en:Method) * | 1989-01-31 | 1990-08-15 | ||
| GB8904182D0 (en) * | 1989-02-23 | 1989-04-05 | Glaxo Canada | Pharmaceutical compositions |
| JPH02141516U (en:Method) * | 1989-04-25 | 1990-11-28 | ||
| US5395939A (en) * | 1993-11-30 | 1995-03-07 | North Carolina State University | Method of making asymmetric de ring intermediates for the synthesis of camptothecin and camptothecin analogs |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8427218D0 (en) * | 1984-10-27 | 1984-12-05 | Scras | Pyridine derivatives |
-
1984
- 1984-10-23 GB GB848426738A patent/GB8426738D0/en active Pending
-
1985
- 1985-10-03 ZA ZA857650A patent/ZA857650B/xx unknown
- 1985-10-03 US US06/783,946 patent/US4610990A/en not_active Expired - Lifetime
- 1985-10-07 GB GB08524709A patent/GB2165845B/en not_active Expired
- 1985-10-09 BE BE0/215703A patent/BE903403A/fr not_active IP Right Cessation
- 1985-10-11 CH CH4402/85A patent/CH665842A5/fr not_active IP Right Cessation
- 1985-10-11 NL NL8502788A patent/NL8502788A/nl not_active Application Discontinuation
- 1985-10-11 AR AR301909A patent/AR240942A1/es active
- 1985-10-15 LU LU86117A patent/LU86117A1/xx unknown
- 1985-10-16 SE SE8504825A patent/SE460904B/sv not_active IP Right Cessation
- 1985-10-20 DZ DZ850233A patent/DZ851A1/fr active
- 1985-10-21 FI FI854088A patent/FI82249C/fi not_active IP Right Cessation
- 1985-10-22 PT PT81351A patent/PT81351B/pt not_active IP Right Cessation
- 1985-10-22 DK DK483185A patent/DK159319C/da not_active IP Right Cessation
- 1985-10-22 MA MA20783A patent/MA20559A1/fr unknown
- 1985-10-22 NO NO854206A patent/NO163777C/no unknown
- 1985-10-22 ES ES548108A patent/ES8609329A1/es not_active Expired
- 1985-10-22 CA CA000493578A patent/CA1286300C/en not_active Expired - Lifetime
- 1985-10-22 IE IE260985A patent/IE58499B1/en not_active IP Right Cessation
- 1985-10-23 JP JP60235511A patent/JPS61106578A/ja active Granted
- 1985-10-23 AT AT0305785A patent/AT393682B/de active
- 1985-10-23 IT IT22597/85A patent/IT1190409B/it active
- 1985-10-23 FR FR858515711A patent/FR2571965B1/fr not_active Expired - Lifetime
- 1985-10-23 FR FR8515710A patent/FR2572075B1/fr not_active Expired
- 1985-10-23 DE DE19853537715 patent/DE3537715A1/de active Granted
- 1985-10-23 OA OA58710A patent/OA08125A/xx unknown
-
1987
- 1987-12-24 MY MYPI87003248A patent/MY102281A/en unknown
-
1988
- 1988-06-09 HK HK443/88A patent/HK44388A/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0026848B1 (de) | Tetralinderivate, ihre Herstellung und Heilmittel, welche diese Verbindungen enthalten | |
| DE3441975A1 (de) | 7-carboxymethoxy-furo-(3,4-c)-pyridin-derivate, verfahren zu deren herstellung und sie enthaltende pharmazeutische zusammensetzung | |
| DE3537715C2 (en:Method) | ||
| DE2605377A1 (de) | 0-aminooxime, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| DE4131584A1 (de) | Imidazolylmethyl-pyridine, ihre herstellung und anwendung als pharmazeutika | |
| DE2359773C2 (en:Method) | ||
| DE3438244C2 (en:Method) | ||
| AT394558B (de) | Verfahren zur herstellung neuer 6-phenaethylaminoalkyl-7-hydroxy-furo-(3,4-c)pyridinderivate | |
| EP0025864A1 (de) | Tetrahydrochinolinderivate, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Zubereitungen | |
| DE2521347C3 (de) | Hydroxylsubstituierte 2-Chlor- a, -(tertbutylaminomethyl)-benzylalkohole, Herstellungsverfahren und Arzneimittel | |
| DE2834107A1 (de) | Benzylalkoholderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel | |
| DE2730593A1 (de) | Neue aminoalkoxybenzofurane, verfahren zur herstellung derselben und diese enthaltende pharmazeutische mittel | |
| DD157799A5 (de) | Verfahren zur herstellung substituierter triarylthiazole | |
| DE2703522C2 (en:Method) | ||
| DE3876546T2 (de) | Ethanon-oxime. | |
| DE2737520A1 (de) | Tetrahydropyridylderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungen | |
| DE1695882B2 (de) | 2-Pyridylmethylamine und Verfahren zu ihrer Herstellung | |
| DE2629756C2 (en:Method) | ||
| DD256695A5 (de) | Verfahren zur herstellung von einem optisch aktiven 2-chlor-12-3/3-dimethylamine-2-methylpropyl/-12h-di-benzo(d,g)(1,3,6)dixazocin | |
| DE2545569B2 (de) | 1,3-dithiacyclopenten-2-ylidenmalonsaeuredialkylester, verfahren zu deren herstellung und diese enthaltende fungizide mittel | |
| DE2650231A1 (de) | Neue imidazolverbindungen, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE3336410A1 (de) | Sulfenamidderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE3513184A1 (de) | 1,3,4-thiadiazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| US4506075A (en) | Process of preparing cardiotonic 3-methyl-4-(4-pyridinyl)benzeneamines | |
| DE1695757C3 (de) | Pyridinmethanolcarbamate und Verfahren zu deren Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |