ES355858A1 - 3-aminoacylamino-thiophens and process for preparing them - Google Patents
3-aminoacylamino-thiophens and process for preparing themInfo
- Publication number
- ES355858A1 ES355858A1 ES355858A ES355858A ES355858A1 ES 355858 A1 ES355858 A1 ES 355858A1 ES 355858 A ES355858 A ES 355858A ES 355858 A ES355858 A ES 355858A ES 355858 A1 ES355858 A1 ES 355858A1
- Authority
- ES
- Spain
- Prior art keywords
- methylthiophene
- carbomethoxy
- reacting
- chloroacetylamino
- amino
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D333/26—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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D333/26—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
- C07D333/36—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Novel 3-aminoacylaminothiophenes of the formula wherein R 1 and R 2 are H, C 1-6 alkyl, optionally substituted by one or more OH of C 1-3 alkoxy groups, C 5-6 cycloalkyl or C 2-4 alkenyl, with the proviso that one of R 1 and R 2 is other than H, or R 1 and R 2 , together with the N atom, may form a saturated 5-7-membered heterocyclic ring, optionally containing O, N or methylimino group R 3 , R 4 and R 5 , each are H, C 1-4 alkyl or carbalkoxy and A is C 1-4 alkylene, and the physiologically tolerable acid addition salts thereof, are prepared by one of the following methods:- (a) By reacting the appropriate 3-halogeno (or alkoxy-, aralkoxy- or aryloxy-) acylaminothiophene with an amine of the formula HN(R 1 )R 2 . (b) By reacting the appropriate 3-aminothiophene or an alkali or alkaline earth metal salt or Grignard compound thereof with an aminocarboxylic acid or reactive derivative thereof of the formula HOOC-A-N(R 1 )R 2 . (c) By dehydrogenating the corresponding 3-aminoacylamino-4,5- or 2,5-dihydrothiophene. (d) By alkylating the corresponding 3- aminoacylaminothiophene of the above general formula wherein R 1 and R 2 are H. (e) By hydrolysing the corresponding 3- aminoacylaminothiophene of the above general formula wherein R 1 is an ester group. (f) By reacting the corresponding 3-aminoacylaminothiophene in which the acyl group is unsaturated with an amine of the formula HN(R 1 )R 2 . (g) By reacting the corresponding 3-isocyanothiophene with an amine of the formula HN(R 1 )R 2 , in the presence of an aliphatic aldehyde containing 1 to 4 carbon atoms. (h) By hydrolysing and decarboxylating the corresponding 3-aminoacylaminothiophene in which R 3 , R 4 and/or R 5 are carbalkoxy groups. 3 - Chloroacetylamino - 2 - carbomethoxy - 4- methylthiophene is obtained by reacting 3-amino- 2 - carbomethoxy - 4 - methylthiophene with chloroacetyl chloride. Similarly 3-chloroacetylamino - 4 - carbomethoxy - 2 - methylthiophene, 3 - chloroacetylamino - 5 - carbomethoxy - 2,4 - dimethylthiophene, 3 - [alpha] - chloropropionylamino - 2 - carbomethoxy - 4 - methylthiophene, 3 - # - chloropropionylamino - 2 - carbomethoxy - 4 - methylthiophene, 3 - chloroacetylamino - 2 - carbethoxy - 4 - methylthiophene, 3 - [alpha] - chloropropionylamino - 4 - methylthiophene, and 3 - # - chloropropionylamino - 4 - methylthiophene are prepared. 3-Chloroacetylaminothiophene is made by reacting chloroacetyl chloride with 3-aminothiophene resulting from the decarboxylation of 3 - amino - 2 - carboxythiophene. By similar processes 3-chloroacetylamino-4-methylthiophene, 3 - amino - 4 - methylthiophene, 3 - chloroacetylamino - 2,4 - dimethylthiophene and 3 - amino- 2,4-dimethylthiophene are obtained. 3 - Isocyano - 2 - carbomethoxy - 4 - methylthiophene is obtained by dehydrating 3-formylamino - 2 - carbomethoxy - 4 - methylthiophene. 3 - Crotonylamino - 4 - methylthiophene is prepared by reacting 3-amino-4-methylthiophene with crotonic acid chloride. N - Benzyloxycarbonyl - n - butylaminoacetylamino - 4 - methylthiophene and N - benzyloxycarbonyl - n - butylaminoacetyl - 5 - carbomethoxy- 2,4-dimethylthiophene are made by reacting N- benzyloxycarbonyl - n - butylaminoacetic acid with 3-amino-4-methylthiophene and 3-amino- 5-carbomethoxy-2,4-dimethylthiophene in the presence of ethyl chloroformate. 3 - n - Butylaminoacetylamino - 2 - carboxy - 4- methylthiophene is obtained by saponification of the corresponding methyl ester. 3 - Diethylaminoacetylamino - 2 - carbomethoxy - 4 - methyl - 4,5 - dihydrothiophene is prepared by reacting diethylamino with 3-chloroacetylamino - 2 - carbomethoxy - 4 - methyl - 4,5- dihydrothiophene resulting from the reaction of 2-carbomethoxy-4-methylthiophenone-(3), with ammonia or ammonium acetate and then with chloroacetyl chloride. Reference has been directed by the Comptroller to Specification 837,086.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1967F0052885 DE1643325B2 (en) | 1967-07-07 | 1967-07-07 | 3-AMINOACYLAMINOTHIOPHENA AND THE METHOD FOR THEIR PRODUCTION |
Publications (1)
Publication Number | Publication Date |
---|---|
ES355858A1 true ES355858A1 (en) | 1970-04-01 |
Family
ID=7105818
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES355858A Expired ES355858A1 (en) | 1967-07-07 | 1968-07-06 | 3-aminoacylamino-thiophens and process for preparing them |
Country Status (14)
Country | Link |
---|---|
AT (7) | AT282613B (en) |
BE (1) | BE717788A (en) |
CH (1) | CH504451A (en) |
CS (7) | CS150587B2 (en) |
DE (1) | DE1643325B2 (en) |
DK (1) | DK120029B (en) |
ES (1) | ES355858A1 (en) |
FI (1) | FI50879C (en) |
FR (2) | FR1584764A (en) |
GB (1) | GB1234833A (en) |
NL (1) | NL156405B (en) |
NO (1) | NO122432B (en) |
SE (1) | SE352639B (en) |
YU (7) | YU33871B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5166346A (en) * | 1987-12-11 | 1992-11-24 | Hoechst Aktiengesellschaft | Process for the preparation of thiophene derivatives and also new dihydrothiophene 1-oxides |
DE4244069A1 (en) * | 1992-12-24 | 1994-06-30 | Hoechst Ag | Cephalosporin salts and process for their preparation |
-
1967
- 1967-07-07 DE DE1967F0052885 patent/DE1643325B2/en active Granted
-
1968
- 1968-07-02 YU YU155668A patent/YU33871B/en unknown
- 1968-07-04 CH CH1001468A patent/CH504451A/en not_active IP Right Cessation
- 1968-07-05 AT AT615869A patent/AT282613B/en not_active IP Right Cessation
- 1968-07-05 NL NL6809539A patent/NL156405B/en not_active IP Right Cessation
- 1968-07-05 AT AT06161/69A patent/AT282615B/en not_active IP Right Cessation
- 1968-07-05 CS CS527868A patent/CS150587B2/cs unknown
- 1968-07-05 AT AT648968A patent/AT281809B/en not_active IP Right Cessation
- 1968-07-05 CS CS528071A patent/CS150589B2/cs unknown
- 1968-07-05 CS CS527668A patent/CS150585B2/cs unknown
- 1968-07-05 DK DK330768A patent/DK120029B/en not_active IP Right Cessation
- 1968-07-05 AT AT616069A patent/AT284833B/en not_active IP Right Cessation
- 1968-07-05 CS CS527968A patent/CS150588B2/cs unknown
- 1968-07-05 CS CS527768A patent/CS150586B2/cs unknown
- 1968-07-05 AT AT615669A patent/AT281810B/en not_active IP Right Cessation
- 1968-07-05 FI FI194668A patent/FI50879C/en active
- 1968-07-05 CS CS498368A patent/CS150583B2/cs unknown
- 1968-07-05 AT AT615769A patent/AT282612B/en not_active IP Right Cessation
- 1968-07-05 CS CS527568A patent/CS150584B2/cs unknown
- 1968-07-05 AT AT615969A patent/AT282614B/en not_active IP Right Cessation
- 1968-07-06 ES ES355858A patent/ES355858A1/en not_active Expired
- 1968-07-08 GB GB3243868A patent/GB1234833A/en not_active Expired
- 1968-07-08 SE SE937268A patent/SE352639B/xx unknown
- 1968-07-08 FR FR1584764D patent/FR1584764A/fr not_active Expired
- 1968-07-08 NO NO271568A patent/NO122432B/no unknown
- 1968-07-08 BE BE717788D patent/BE717788A/xx not_active IP Right Cessation
- 1968-10-04 FR FR168764A patent/FR8214M/fr not_active Expired
-
1973
- 1973-09-27 YU YU256273A patent/YU33963B/en unknown
- 1973-09-27 YU YU256373A patent/YU34043B/en unknown
- 1973-09-27 YU YU256073A patent/YU33961B/en unknown
- 1973-09-27 YU YU256173A patent/YU33962B/en unknown
- 1973-09-27 YU YU256573A patent/YU33965B/en unknown
- 1973-09-27 YU YU256473A patent/YU33964B/en unknown
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