KR840000536A - 2-(2-티에닐)-및 (3-티에닐)- 에틸아민의 제조방법 - Google Patents
2-(2-티에닐)-및 (3-티에닐)- 에틸아민의 제조방법 Download PDFInfo
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- KR840000536A KR840000536A KR1019820002912A KR820002912A KR840000536A KR 840000536 A KR840000536 A KR 840000536A KR 1019820002912 A KR1019820002912 A KR 1019820002912A KR 820002912 A KR820002912 A KR 820002912A KR 840000536 A KR840000536 A KR 840000536A
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- 238000004519 manufacturing process Methods 0.000 title claims 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 title claims 2
- DTDHODSOKFHWQE-UHFFFAOYSA-N n-ethylthiophen-3-amine Chemical compound CCNC=1C=CSC=1 DTDHODSOKFHWQE-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 239000002585 base Substances 0.000 claims 5
- 150000001728 carbonyl compounds Chemical class 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- -1 nitro, carboxy, cyano, amino Chemical group 0.000 claims 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 150000002903 organophosphorus compounds Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910010277 boron hydride Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 150000004292 cyclic ethers Chemical class 0.000 claims 1
- 125000004986 diarylamino group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 150000002681 magnesium compounds Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 150000002901 organomagnesium compounds Chemical class 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 150000003388 sodium compounds Chemical class 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
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- C07F9/02—Phosphorus compounds
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- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
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- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
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Claims (34)
- 다음 일반식 (Ⅰ)으로 표시되는 2-(2-티에닐)-과 -(3-티에닐)에틸아민의 제조방법에 있어서,
-
- (상기식에서 R1은 2-, 3-, 4- 또는 5-위치에서 수소원자, 할로겐원자, 니트로, 카르복시, 시아노, 아미노 또는 직쇄 또는 분지쇄 알킬 또는 알콕시기와 할로, 니트로, 시아노, 아미노, 카르복시, 알킬, 알콕시 또는 페닐기에 의하여 임의로 모노- 또는 폴리-치환된 복소환식 또는 비-복소환식 방향족기를 나타내고, 2- 또는 3-위치에 연결된 아미노 에틸에서 R2, R3와 R4는 수소원자 또는 할로, 시아노, 아미노, 카르복시, 알킬, 알콕시 또는 페닐기에 의하여 임의로 치환된 복소환식 또는 비-복소환식 방향족기를 나타내고, Ar은 알킬 또는 페닐기에 의하여 임의로 모노- 또는 폴리- 치환된 복소환식 또는 비-복소환식 방향족기를 나타낸다.
- 다음 일반식 (Ⅱ)으로 표시되는 유도체(Ⅱ) :
-
- (상기식에서 R3는 상술한 의미같고, X와 Y는 서로 각각 알킬, 알콕시, 아릴, 아릴옥시, 디알킬아미노 또는 디아릴아미노기를 나타낸다.)
- 를 다음 일반식 (Ⅲ)으로 표시되는 카르보닐 화합물 :
-
- (상기식에서 Ar과 R4는 전술한 바와 같다)
- 과 축합시켜서 다음 일반식 (Ⅳ)의 유도체를 제조하고 ;
-
- (상기식에서 X, Y, Ar, R4와 R3는 전술한 바와 같다)
- 상기 화합물(Ⅳ)을 일반식 BM의 염기와 처리하여 다음 일반식 (V)의 카트바니온을 제조하고 ;
-
- 상기 일반식 (Ⅴ)의 카르바니온을 다음 일반식 (Ⅶ)의 카르보닐유도체 :
-
- (상기식에서 R1과 R2는 전술한 바와 같다.)
- 와 반응시켜서 다음 일반식 (Ⅷ)으로 표시되는 화합물을 제조하고 :
-
- (상기식에서 R1, R2, R3, R4와 Ar은 전술한 바와 같다.)
- 상기 화합물 (Ⅷ)을 환원제와 치리하여 일반식 (Ⅰ)으로 표시되는 화합물을 제조함을 특징으로 하는 상기 일반식 (Ⅰ)의 화합물의 제조방법.
- 청구범위 1에 있어서, R1, R2, R3, R4와 Ar로 언급한 복소환식 또는 비-복소환식 방향족기를 티에닐, 푸릴, 피리딜, 페닐과 나프틸로부터 선택함을 특징으로 하는 상기 제조방법.
- 청구범위 1에 있어서, 유기인 화합물 (Ⅱ)과 카르보닐 화합물 (Ⅲ)을 축합반응 시킬 때 후자가 케톤(R4=H)인 경우, 파라톨루엔 설폰산과 같은 무기산 또는 유기산의 존재하에 촉매작용시킴을 특징으로하는 상기 제조방법.
- 청구범위 1-3 중 어느 하나에 있어서, 상기 염기의 존재하에서 카르바니온의 제조를 -78℃와 +100℃의 온도에서 행함을 특징으로 하는 상기 제조방법.
- 청구범위 4에서, M가 알카리 또는 알카리토류 금속이고, B가 수소, 히드록시, 아미노, 모노- 또는 디알킬아미노, 직쇄 또는 분지쇄알킬 또는 직쇄나 분지쇄알콕시에 상응하는 음전하기로부터 선택된 카르바니온이거나 염기 BM가 유기 마그네슘 화합물 또는 유기 나트륨 화합물임을 특징으로 하는 상기 제조방법.
- 청구범위 5에 있어서, M가 나트륨, 리륨, 칼륨과 마그네슘으로부터 선택한 금속임을 특징으로하는 상기 제조방법.
- 청구범위 5에 있어서, 사용된 염기가 알카리 금속 수소화물, 유기 마그네슘 화합물, 알카리 금속과 알카리토류 금속 알콕사이드와 히드록사이드로부터 선택함을 특징으로 하는 상기 제조방법.
- 청구범위 4-7에 있어서, 직쇄와 환식 에테르, 방향족 탄화수소, 알콜, 아미드와 설폭 사이드에서 반응을 행함을 특징으로 하는 상기 제조방법.
- 청구범위 8에 있어서, 테트라하이드로푸란, 벤젠과 디메틸설폭사이드로부터 선택된 유기용매에서 반응을 행함을 특징으로 하는 상기 제조방법.
- 청구범위 4-7 중 어느 하나에 있어서, 상기 카르바니온의 제조를 염기의 성질에 따라, 낮은 온도의 범위내에서 선택된 온도에서 행함을 특징으로 하는 상기 제조방법.
- 청구범위 1-10 중 어느 하나에 있어서, 카르바니온 (Ⅴ)과 카르보닐 유도체 (Ⅶ) 사이의 반응을 -78℃~100℃의 온도에서 행함을 특징으로 하는 상기 제조방법.
- 청구범위 1-11 중 어느 하나에 있어서, 화합물 (Ⅲ)의 수소화 반응을 수소화 붕소나트륨, 수소화 붕소칼륨과 같은 알카리금속 붕소수소화물로 행함을 특징으로 하는 상기 제조방법.
- 청구범위 12에 있어서, 반응을 테트라하이드로푸란, 디옥산, 메탄올 또는 에탄올과 같은 유기용매에서 행함을 특징으로하는 상기 제조방법.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8113062 | 1981-06-30 | ||
| FR8113062A FR2508453A1 (fr) | 1981-06-30 | 1981-06-30 | Procede de preparation de derives des (thienyl-2)- et thienyl-3)-2 ethylamines et produits ainsi obtenus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840000536A true KR840000536A (ko) | 1984-02-25 |
Family
ID=9260129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019820002912A KR840000536A (ko) | 1981-06-30 | 1982-06-30 | 2-(2-티에닐)-및 (3-티에닐)- 에틸아민의 제조방법 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4482718A (ko) |
| EP (1) | EP0068978B1 (ko) |
| JP (1) | JPS5810574A (ko) |
| KR (1) | KR840000536A (ko) |
| AT (1) | ATE21897T1 (ko) |
| AU (1) | AU566802B2 (ko) |
| CA (1) | CA1205810A (ko) |
| CS (1) | CS248028B2 (ko) |
| DD (1) | DD206377A5 (ko) |
| DE (1) | DE3273015D1 (ko) |
| DK (1) | DK286682A (ko) |
| ES (1) | ES514221A0 (ko) |
| FI (1) | FI822315L (ko) |
| FR (1) | FR2508453A1 (ko) |
| GR (1) | GR76496B (ko) |
| HU (1) | HU194860B (ko) |
| IE (1) | IE53228B1 (ko) |
| IL (1) | IL65980A (ko) |
| NO (1) | NO155136C (ko) |
| NZ (1) | NZ200852A (ko) |
| PT (1) | PT75152B (ko) |
| SU (1) | SU1148563A3 (ko) |
| YU (1) | YU143382A (ko) |
| ZA (1) | ZA824624B (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2508454A1 (fr) * | 1981-06-30 | 1982-12-31 | Sanofi Sa | Procede de preparation de derives des (thienyl-2)- et (thienyl-3)-2 ethylamines et produits ainsi obtenus |
| CA1242718A (en) * | 1983-11-21 | 1988-10-04 | John R. Carson | Acetylene derivatives and methods for the treatment of hypertension and angina |
| CA1292747C (en) * | 1983-11-21 | 1991-12-03 | John Robert Carson | Aralykyl (arylethynyl) aralkyl amines and their use as vasodilators and antihypertensives |
| FR2622191B1 (fr) * | 1987-10-22 | 1991-06-21 | Sanofi Sa | Procede de preparation de la n-(chloro-2 benzyl)-2 ethylamine et produits intermediaires dans cette preparation |
| JPH0283380A (ja) * | 1988-09-21 | 1990-03-23 | Kotobuki Seiyaku Kk | 新規ジアミン誘導体、抗不整脈剤及びその製法 |
| US4900539A (en) * | 1988-12-22 | 1990-02-13 | The United States Of America As Represented By The United States Department Of Energy | Radiohalogenated thienylethylamine derivatives for evaluating local cerebral blood flow |
| EP0596120A4 (en) * | 1991-08-09 | 1994-07-06 | Yoshitomi Pharmaceutical | Thiophene compound. |
| US9012660B2 (en) * | 2011-08-17 | 2015-04-21 | Shandong Luye Pharmaceutical Co., Ltd. | 5,6,7,8-tetrahydro-6-[N,N-bis[(2-thienyl)ethyl]] amino-1-naphthol, and preparing method and use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2983729A (en) * | 1958-04-30 | 1961-05-09 | Monsanto Chemicals | Preparation of 5-halothienyl amines |
| FR2300090A1 (fr) * | 1975-02-07 | 1976-09-03 | Parcor | Procede de preparation de derives de la thienopyridine |
| US4127580A (en) * | 1975-02-07 | 1978-11-28 | Parcor | Process for the preparation of thieno-pyridine derivatives |
| FR2315274A1 (fr) * | 1975-06-27 | 1977-01-21 | Parcor | Nouveaux derives de la thieno (2,3-c) pyridine, leur preparation et leurs applications |
| IT1082336B (it) * | 1977-01-27 | 1985-05-21 | Medea Res Srl | Processo per la preparazione della 5.2.clorobenzil.4 5 6 7.tetraidro tien 3 2.c.piridina |
-
1981
- 1981-06-30 FR FR8113062A patent/FR2508453A1/fr active Granted
-
1982
- 1982-06-01 IE IE1310/82A patent/IE53228B1/en unknown
- 1982-06-04 NZ NZ200852A patent/NZ200852A/xx unknown
- 1982-06-06 IL IL65980A patent/IL65980A/xx unknown
- 1982-06-09 GR GR68374A patent/GR76496B/el unknown
- 1982-06-10 ES ES514221A patent/ES514221A0/es active Granted
- 1982-06-10 AU AU84755/82A patent/AU566802B2/en not_active Ceased
- 1982-06-16 AT AT82401095T patent/ATE21897T1/de active
- 1982-06-16 EP EP82401095A patent/EP0068978B1/fr not_active Expired
- 1982-06-16 DE DE8282401095T patent/DE3273015D1/de not_active Expired
- 1982-06-25 DK DK286682A patent/DK286682A/da not_active Application Discontinuation
- 1982-06-29 NO NO822224A patent/NO155136C/no unknown
- 1982-06-29 SU SU823459385A patent/SU1148563A3/ru active
- 1982-06-29 PT PT75152A patent/PT75152B/pt not_active IP Right Cessation
- 1982-06-29 US US06/393,387 patent/US4482718A/en not_active Expired - Fee Related
- 1982-06-29 FI FI822315A patent/FI822315L/fi not_active Application Discontinuation
- 1982-06-29 CS CS824895A patent/CS248028B2/cs unknown
- 1982-06-29 DD DD82241200A patent/DD206377A5/de unknown
- 1982-06-29 ZA ZA824624A patent/ZA824624B/xx unknown
- 1982-06-29 HU HU822107A patent/HU194860B/hu unknown
- 1982-06-29 CA CA000406290A patent/CA1205810A/en not_active Expired
- 1982-06-30 KR KR1019820002912A patent/KR840000536A/ko unknown
- 1982-06-30 JP JP57113843A patent/JPS5810574A/ja active Pending
- 1982-06-30 YU YU01433/82A patent/YU143382A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU8475582A (en) | 1983-01-06 |
| IE821310L (en) | 1982-12-30 |
| HU194860B (en) | 1988-03-28 |
| NO155136C (no) | 1987-02-18 |
| IL65980A (en) | 1985-12-31 |
| NO822224L (no) | 1983-01-03 |
| FR2508453B1 (ko) | 1983-12-23 |
| FI822315L (fi) | 1982-12-31 |
| ATE21897T1 (de) | 1986-09-15 |
| CS248028B2 (en) | 1987-01-15 |
| US4482718A (en) | 1984-11-13 |
| ES8305349A1 (es) | 1983-04-01 |
| GR76496B (ko) | 1984-08-10 |
| DK286682A (da) | 1982-12-31 |
| EP0068978B1 (fr) | 1986-09-03 |
| PT75152B (fr) | 1984-05-29 |
| PT75152A (fr) | 1982-07-01 |
| NO155136B (no) | 1986-11-10 |
| CA1205810A (en) | 1986-06-10 |
| NZ200852A (en) | 1985-09-13 |
| ZA824624B (en) | 1983-04-27 |
| FR2508453A1 (fr) | 1982-12-31 |
| AU566802B2 (en) | 1987-10-29 |
| ES514221A0 (es) | 1983-04-01 |
| YU143382A (en) | 1984-12-31 |
| IL65980A0 (en) | 1982-09-30 |
| IE53228B1 (en) | 1988-09-14 |
| SU1148563A3 (ru) | 1985-03-30 |
| JPS5810574A (ja) | 1983-01-21 |
| EP0068978A1 (fr) | 1983-01-05 |
| FI822315A0 (fi) | 1982-06-29 |
| DE3273015D1 (en) | 1986-10-09 |
| DD206377A5 (de) | 1984-01-25 |
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