SU886743A3 - Способ получени солей щелочных металлов производных 2-пиридил- или 2-пиримидиламинобензойной кислоты - Google Patents
Способ получени солей щелочных металлов производных 2-пиридил- или 2-пиримидиламинобензойной кислоты Download PDFInfo
- Publication number
- SU886743A3 SU886743A3 SU792765447A SU2765447A SU886743A3 SU 886743 A3 SU886743 A3 SU 886743A3 SU 792765447 A SU792765447 A SU 792765447A SU 2765447 A SU2765447 A SU 2765447A SU 886743 A3 SU886743 A3 SU 886743A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- amino
- tetrazol
- benzene ring
- hydrogen
- pyridyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 150000003839 salts Chemical class 0.000 title abstract description 6
- 239000002253 acid Substances 0.000 title description 3
- 229910052751 metal Inorganic materials 0.000 title description 2
- 239000002184 metal Substances 0.000 title description 2
- -1 or (b) -CO-R4 Chemical group 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 5
- 239000001257 hydrogen Substances 0.000 claims abstract 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- NNTYAXNEQRSVAQ-UHFFFAOYSA-N 2-(pyrimidin-2-ylamino)benzoic acid Chemical class OC(=O)C1=CC=CC=C1NC1=NC=CC=N1 NNTYAXNEQRSVAQ-UHFFFAOYSA-N 0.000 claims 1
- 206010039509 Scab Diseases 0.000 claims 1
- 239000000043 antiallergic agent Substances 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 abstract 2
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- OKXPYKHKJCATPX-UHFFFAOYSA-N quinazoline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=NC=C21 OKXPYKHKJCATPX-UHFFFAOYSA-N 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- OPWGQSSVKMOEQO-UHFFFAOYSA-N 4-(quinolin-2-ylamino)benzene-1,3-dicarboxylic acid Chemical compound N1=C(C=CC2=CC=CC=C12)NC1=C(C=C(C(=O)O)C=C1)C(=O)O OPWGQSSVKMOEQO-UHFFFAOYSA-N 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- JCAZHTTXKYZJCC-UHFFFAOYSA-N N1N=NN=C1C1=NC2=CC=CC=C2C=N1 Chemical compound N1N=NN=C1C1=NC2=CC=CC=C2C=N1 JCAZHTTXKYZJCC-UHFFFAOYSA-N 0.000 description 1
- 241000219422 Urtica Species 0.000 description 1
- 235000009108 Urtica dioica Nutrition 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Medicinal Preparation (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ СОЛЕЙ ЩЕЛОЧНЫХ МЕТАЛЛОВ ПРОИЗВОДНЫХ
2-ПИРИДШ1- ИЛИ а-пиримидилАминоБЕнзойной кислоты 38 подвергают вазимодействию со щелочью и целевой продукт выдел ют в виде со ли щелочного металла. Целевые продукты могут примен тьс дл терапевтических целей, например, в качестве реагентов антиаллергического действи , дл лечени аллергических болезней, таких как астма сенна лихорадка, конъюнктивит, крапивна лихорадка, экземы, атонический дерйатйт. Новые соединени , кроме того, имеют бронхорасшир ющие и сосудорасшир ющее действи . Пример 1. Динатриева соль 4-(2-пиридиламино -изофталевой кислоты . 5,24 г цатриевой соли ll-H-11-оксо-пиридо- 2 ,1-в хиназолин-2-карбоновой кислоты и 20 мл 1 н; едкого натра йагревают на вод ной бане в течение 1 ч. Из полученного прозрачного желтого раствора удал ют воду в вид азеотропа с хлороформом. Полученные кристаллы суспендируют в небольшом количестве простого эфира, фильт уют и сушат в вакууме при . Выход 4,86 г (72% от теоретического. Вычислено, %: С 46,15; Н 55; N 8,28; 10,65. Найдено, %: С 46,04; Н 3,34|: МБ, 15; 11,1&. УФ-сиектрГЛупаХ логе4,18 4,30 Пример 2. Ди атриева соль 2- (2-пиридиламинс) -5- (. 1 Н-тетразол-5г-ил )-бензойной кислоты. 8 г П-Н-11-оксопиридо-f 2,1-BJ-2- (1Н-тетразол-5-ил -хиназолина и 60,6 мл I Н. едкого натра нагревают цо 70 С в течение 2 ч, отгон ют воду и кристаллы суспендируют в небольшом количестве простого эфира, фильтруют ц сушат при в вакууме. Выход г { 76% от теоретического}. Вычислено %: С 41,05; Н 3,68; N22,10. ;,HgW. X ЗН,,0 Ийдеко, %: С 41,98; Н 3,54; И 22,18. УФ-спектр:Ху ЯХ,нм 290 317 доге 4,24 4,27 Пример 3. Дикалиева соль 4-(. 2-пирндиламино) -изофталевой кислоты . 5,56 г (о,02 мол калиевой сол 11-Н-1 Ноксо-пиридо-р, I-B хиназолин-2-карбоновой кислоты нагревают в течение 1 ч с 20 мл едкого кали. Из соответств щего раствора азеотроцно удал ют воду. Остаток суспевдйруют в простом эфире, отсасывают и сущат при 60 С. Выход соединени составл ет 85% УФ-спектр:А,„ат1НМ 288 328 лог g 4,18 4,30 Аналогично получают натриевую соль соединений, приведенных в таблице.
f
НН-
(JOOdH;
4,18
80 4,40
4-(2-Хинолиниламино)изофталева кислота
Нз y xx-CJOOH .j j ss x CJOOH
чАкн-4 ,25 84
320
лева кислота 4-( 5-Ацетамидо-.2- еН -пиридиАамино ) -изо-, -пмпыпыН минг 1 фталева кислота
Йродолжение таблицы ( J-NK.,, HDOd,C.OOH, , иI TVtи .Ло 4.25 .-Л 4,30 . l MoHo-N-(ш-тетраf золгЗ-ил -карбоксамид 4-(2-пиридилWx JJHамино )-изофталевЬй ,кислоты
Hood,,,/г
VCOOH
jT
f -NH886743
8 Продолжение таблицы.
Hood
4,30 75
325
54,6
с ООН
4,18
78,4 4,30
сбон
2,24
290
65, Р:F- K b-iJH-f 11 к
Claims (1)
- Формула изобретениСпособ получени солей щелочных металлов производных 2-пиридйл- или 2-пиримидиламинобензойной кислоты общей формулы IСРОКбензольное кольцо или группа -CO-R в 4 или 5 положении кольца;rpyjtina -СО-ДЧ тетразол-5-ил, циан в 4 или 5 положении бензольного Кольца шш, если R означает группу -COR, то R - водород, метил, метокси или конденсированное бензольное кольцо;ft - окси, амино, гидроксиамино, тетразол-5-ил-амино или метокси, отличающийс тем, что соедииение общей формулы 11в которойА - группа гСН- илиR - водород, метил, метокси, амино, ацетамино, конденсированное.988674 . ,0гдеЛ yfl и А имеют указанные значе-Источники информации,ни , подвергают взаимодействию со ще- . прин тые во внимание при экспертизе лочью и целевой продукт выдел ют в 1. Патент Великобритании № 1064259, виде соли щелочного металла.кл. С 071 31/24, опублик. 1967.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772735919 DE2735919A1 (de) | 1977-08-10 | 1977-08-10 | Neue 2-pyridyl- und 2-pyrimidylaminobenzoesaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU886743A3 true SU886743A3 (ru) | 1981-11-30 |
Family
ID=6016013
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782646404A SU735168A3 (ru) | 1977-08-10 | 1978-08-08 | Способ получени циклической карбоновой кислоты или ее соли |
| SU792765447A SU886743A3 (ru) | 1977-08-10 | 1979-05-21 | Способ получени солей щелочных металлов производных 2-пиридил- или 2-пиримидиламинобензойной кислоты |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782646404A SU735168A3 (ru) | 1977-08-10 | 1978-08-08 | Способ получени циклической карбоновой кислоты или ее соли |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4241068A (ru) |
| JP (1) | JPS5430177A (ru) |
| AT (1) | AT370415B (ru) |
| AU (1) | AU520240B2 (ru) |
| BE (1) | BE869640A (ru) |
| BG (1) | BG30472A1 (ru) |
| CA (1) | CA1111037A (ru) |
| CH (1) | CH649289A5 (ru) |
| CS (1) | CS202506B2 (ru) |
| DD (1) | DD140351A5 (ru) |
| DE (1) | DE2735919A1 (ru) |
| DK (1) | DK148019C (ru) |
| ES (5) | ES472143A1 (ru) |
| FI (1) | FI71555C (ru) |
| FR (1) | FR2400017A1 (ru) |
| GB (1) | GB2002764B (ru) |
| GR (1) | GR65024B (ru) |
| HU (1) | HU179933B (ru) |
| IE (1) | IE47228B1 (ru) |
| IT (1) | IT1107960B (ru) |
| LU (1) | LU80094A1 (ru) |
| MX (1) | MX5672E (ru) |
| NL (1) | NL7808319A (ru) |
| NO (1) | NO152605C (ru) |
| NZ (1) | NZ188101A (ru) |
| PH (1) | PH19117A (ru) |
| PL (2) | PL115889B1 (ru) |
| PT (1) | PT68407A (ru) |
| SE (1) | SE444170B (ru) |
| SU (2) | SU735168A3 (ru) |
| YU (1) | YU40832B (ru) |
| ZA (1) | ZA784501B (ru) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3100516A1 (de) * | 1981-01-10 | 1982-08-12 | C.H. Boehringer Sohn, 6507 Ingelheim | Pyridylaminobenzoesaeuren, ihre herstellung und verwendung |
| FR2533567A1 (fr) * | 1982-09-23 | 1984-03-30 | Ki I Farmakologii | 2-(orthocarboxyphenylamino)-6h-pyrimido (2,1-b)-quinazolone-6 et ses derives, leur procede de preparation et leur application therapeutique |
| US4610991A (en) * | 1983-04-18 | 1986-09-09 | Sterling Drug Inc. | Antihypertensive pyridylaminobenzamide compounds |
| JPS60100559A (ja) * | 1983-11-05 | 1985-06-04 | Morishita Seiyaku Kk | ２−アニリノ−１，６−ジヒドロ−６−オキソ−５−ピリミジンカルボン酸誘導体，その製法及び該化合物を含有する抗アレルギ−剤 |
| US4584379A (en) * | 1985-01-22 | 1986-04-22 | Merrell Dow Pharmaceuticals Inc. | Isoquinoline thromboxane synthetase inhibitors |
| EP0219308B1 (en) * | 1985-10-16 | 1991-10-23 | Merck Frosst Canada Inc. | 2-substituted quinolines |
| GB9615950D0 (en) * | 1996-07-30 | 1996-09-11 | Univ Warwick | Variable reluctance machines |
| US6022884A (en) | 1997-11-07 | 2000-02-08 | Amgen Inc. | Substituted pyridine compounds and methods of use |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1064259A (en) * | 1963-12-19 | 1967-04-05 | Union Pharma Scient Appl | New derivatives of 2-anilino-nicotinic acid and process for their preparation |
| GB1162287A (en) * | 1967-11-07 | 1969-08-20 | Union Pharma Scient Appl | New Salts of 2-Anilino-Nicotinic Acids |
| GB1264798A (ru) * | 1968-07-10 | 1972-02-23 | ||
| ES416847A1 (es) * | 1973-07-12 | 1976-03-01 | Hermes Sa Lab | Procedimiento para la obtencion de derivados del acido ni- cotinico. |
-
1977
- 1977-08-10 DE DE19772735919 patent/DE2735919A1/de active Granted
-
1978
- 1978-06-27 FI FI782039A patent/FI71555C/fi not_active IP Right Cessation
- 1978-07-07 GR GR56729A patent/GR65024B/el unknown
- 1978-07-28 ES ES472143A patent/ES472143A1/es not_active Expired
- 1978-07-28 AT AT0549278A patent/AT370415B/de not_active IP Right Cessation
- 1978-07-31 PH PH21447A patent/PH19117A/en unknown
- 1978-08-07 CH CH8381/78A patent/CH649289A5/de not_active IP Right Cessation
- 1978-08-07 MX MX787292U patent/MX5672E/es unknown
- 1978-08-08 DD DD78207180A patent/DD140351A5/de unknown
- 1978-08-08 SU SU782646404A patent/SU735168A3/ru active
- 1978-08-08 LU LU80094A patent/LU80094A1/de unknown
- 1978-08-08 IT IT50642/78A patent/IT1107960B/it active
- 1978-08-08 BG BG7840623A patent/BG30472A1/xx unknown
- 1978-08-09 BE BE78189801A patent/BE869640A/xx not_active IP Right Cessation
- 1978-08-09 DK DK351978A patent/DK148019C/da not_active IP Right Cessation
- 1978-08-09 SE SE7808530A patent/SE444170B/sv not_active IP Right Cessation
- 1978-08-09 AU AU38772/78A patent/AU520240B2/en not_active Expired
- 1978-08-09 JP JP9626278A patent/JPS5430177A/ja active Granted
- 1978-08-09 HU HU78BO1727A patent/HU179933B/hu not_active IP Right Cessation
- 1978-08-09 NO NO782707A patent/NO152605C/no unknown
- 1978-08-09 IE IE1618/78A patent/IE47228B1/en unknown
- 1978-08-09 NZ NZ188101A patent/NZ188101A/xx unknown
- 1978-08-09 ZA ZA784501A patent/ZA784501B/xx unknown
- 1978-08-09 PT PT68407A patent/PT68407A/pt unknown
- 1978-08-09 CA CA308,978A patent/CA1111037A/en not_active Expired
- 1978-08-09 NL NL787808319A patent/NL7808319A/xx not_active Application Discontinuation
- 1978-08-09 YU YU1916/78A patent/YU40832B/xx unknown
- 1978-08-09 PL PL1978215270A patent/PL115889B1/pl unknown
- 1978-08-09 GB GB7832731A patent/GB2002764B/en not_active Expired
- 1978-08-09 CS CS785205A patent/CS202506B2/cs unknown
- 1978-08-09 PL PL1978208942A patent/PL115778B1/pl unknown
- 1978-08-10 FR FR7823617A patent/FR2400017A1/fr active Granted
- 1978-11-28 ES ES475457A patent/ES475457A1/es not_active Expired
- 1978-11-28 ES ES475456A patent/ES475456A1/es not_active Expired
-
1979
- 1979-05-16 ES ES480622A patent/ES480622A1/es not_active Expired
- 1979-05-16 ES ES480623A patent/ES480623A1/es not_active Expired
- 1979-05-21 SU SU792765447A patent/SU886743A3/ru active
- 1979-08-07 US US06/064,355 patent/US4241068A/en not_active Expired - Lifetime
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