GB1310046A - Process for the manufacture of thiazacyclic amino compounds - Google Patents
Process for the manufacture of thiazacyclic amino compoundsInfo
- Publication number
- GB1310046A GB1310046A GB3214170A GB3214170A GB1310046A GB 1310046 A GB1310046 A GB 1310046A GB 3214170 A GB3214170 A GB 3214170A GB 3214170 A GB3214170 A GB 3214170A GB 1310046 A GB1310046 A GB 1310046A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penam
- dimethyl
- amino
- phenylacetylamino
- compounds
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- -1 2,2,2 - trichloroethoxycarbonylamino Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 2
- 150000002463 imidates Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- XCMOJCDROUHGPL-NJEKYYFSSA-N (4-methoxyphenyl)methyl N-[(5R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbamate Chemical compound CC1(S[C@H]2N(C1NC(=O)OCC1=CC=C(C=C1)OC)C(C2NC(COC2=CC=CC=C2)=O)=O)C XCMOJCDROUHGPL-NJEKYYFSSA-N 0.000 abstract 1
- GYCAGDQZQWRSPQ-KOHJWAIASA-N (5R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl azide Chemical compound CC1(S[C@H]2N(C1C(=O)N=[N+]=[N-])C(C2NC(CC1=CC=CC=C1)=O)=O)C GYCAGDQZQWRSPQ-KOHJWAIASA-N 0.000 abstract 1
- XVWJOHNEPKYPJZ-HDDMYIMNSA-N 2,2,2-trichloroethyl N-[(5R)-3,3-dimethyl-6-[(2-methylpropan-2-yl)oxycarbonylamino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbamate Chemical compound C(C)(C)(C)OC(=O)NC1[C@@H]2N(C(C(S2)(C)C)NC(=O)OCC(Cl)(Cl)Cl)C1=O XVWJOHNEPKYPJZ-HDDMYIMNSA-N 0.000 abstract 1
- SZBOSAWQTVKDME-HNFVBEJKSA-N 2,2,2-trichloroethyl N-[(5R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbamate Chemical compound CC1(S[C@H]2N(C1NC(=O)OCC(Cl)(Cl)Cl)C(C2NC(CC2=CC=CC=C2)=O)=O)C SZBOSAWQTVKDME-HNFVBEJKSA-N 0.000 abstract 1
- MJWJGFYNCOHKNE-GPDKUZCWSA-N 2,2,2-trichloroethyl N-[(5R)-6-(carbonochloridoylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbamate Chemical compound ClC(=O)NC1[C@@H]2N(C(C(S2)(C)C)NC(=O)OCC(Cl)(Cl)Cl)C1=O MJWJGFYNCOHKNE-GPDKUZCWSA-N 0.000 abstract 1
- KPVWCQWKWYWWHW-GPDKUZCWSA-N 2,2,2-trichloroethyl N-[(5R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbamate Chemical compound NC1[C@@H]2N(C(C(S2)(C)C)NC(=O)OCC(Cl)(Cl)Cl)C1=O KPVWCQWKWYWWHW-GPDKUZCWSA-N 0.000 abstract 1
- DEVXHDQHEVYCMQ-OGVSOVDVSA-N 2-bromoethyl N-[(5R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbamate Chemical compound BrCCOC(=O)NC1C(S[C@H]2N1C(C2NC(CC2=CC=CC=C2)=O)=O)(C)C DEVXHDQHEVYCMQ-OGVSOVDVSA-N 0.000 abstract 1
- FFUNMOICFSOTPN-OGVSOVDVSA-N 2-iodoethyl N-[(5R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbamate Chemical compound ICCOC(=O)NC1C(S[C@H]2N1C(C2NC(CC2=CC=CC=C2)=O)=O)(C)C FFUNMOICFSOTPN-OGVSOVDVSA-N 0.000 abstract 1
- OABPFANFTIUUSB-LXBRNSGXSA-N 2-iodoethyl N-[(5R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbamate Chemical compound NC1[C@@H]2N(C(C(S2)(C)C)NC(=O)OCCI)C1=O OABPFANFTIUUSB-LXBRNSGXSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- TZBWCBARUNPGFL-HNFVBEJKSA-N N-[(5R)-2-isocyanato-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenoxyacetamide Chemical compound N(=C=O)C1C(S[C@H]2N1C(C2NC(COC2=CC=CC=C2)=O)=O)(C)C TZBWCBARUNPGFL-HNFVBEJKSA-N 0.000 abstract 1
- FEATXSQBVJKPOH-HNFVBEJKSA-N N-[(5R)-2-isocyanato-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylacetamide Chemical compound N(=C=O)C1C(S[C@H]2N1C(C2NC(CC2=CC=CC=C2)=O)=O)(C)C FEATXSQBVJKPOH-HNFVBEJKSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical group [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000002496 iodine Chemical class 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- KHCLLFBJDREANG-NJEKYYFSSA-N phenacyl N-[(5R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbamate Chemical compound CC1(S[C@H]2N(C1NC(=O)OCC(=O)C1=CC=CC=C1)C(C2NC(CC2=CC=CC=C2)=O)=O)C KHCLLFBJDREANG-NJEKYYFSSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1037469 | 1969-07-08 | ||
| CH1767069A CH563397A5 (en) | 1969-11-27 | 1969-11-27 | Prepn of amino cpds having pharmacological - properties |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1310046A true GB1310046A (en) | 1973-03-14 |
Family
ID=25706567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3214170A Expired GB1310046A (en) | 1969-07-08 | 1970-07-02 | Process for the manufacture of thiazacyclic amino compounds |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5013798B1 (https=) |
| AR (1) | AR193964A1 (https=) |
| AT (1) | AT299450B (https=) |
| BE (1) | BE753091A (https=) |
| CA (1) | CA921906A (https=) |
| ES (1) | ES381471A2 (https=) |
| FR (1) | FR2059491B1 (https=) |
| GB (1) | GB1310046A (https=) |
| HU (1) | HU162228B (https=) |
| NL (1) | NL7010034A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6058078U (ja) * | 1983-09-30 | 1985-04-23 | 野田 弘 | 線香立て |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1394820A (fr) * | 1964-02-13 | 1965-04-09 | Ciba Geigy | Nouveau procédé de préparation de composés aminés, en particulier de l'acide 7-amino-céphalosporanique |
| DE1935638A1 (de) * | 1968-07-23 | 1970-01-29 | Ciba Geigy | Acyloxyalkylmercaptoverbindungen |
| DE1935970A1 (de) * | 1968-07-23 | 1970-01-29 | Ciba Geigy | Oxyessigsaeureverbindungen |
| DE1935640A1 (de) * | 1968-07-23 | 1970-03-05 | Ciba Geigy | Alkenylmercaptoverbindungen |
| US3705160A (en) * | 1968-07-23 | 1972-12-05 | Ciba Geigy Corp | Thiazacyclic hydroxy compounds and process for their manufacture |
| DE1935459A1 (de) * | 1968-07-23 | 1970-01-29 | Ciba Geigy | Carbinolalkylmercaptoverbindungen |
-
1970
- 1970-07-02 GB GB3214170A patent/GB1310046A/en not_active Expired
- 1970-07-02 FR FR7024604A patent/FR2059491B1/fr not_active Expired
- 1970-07-06 ES ES381471A patent/ES381471A2/es not_active Expired
- 1970-07-07 CA CA087472A patent/CA921906A/en not_active Expired
- 1970-07-07 AT AT613670A patent/AT299450B/de not_active IP Right Cessation
- 1970-07-07 NL NL7010034A patent/NL7010034A/xx unknown
- 1970-07-07 BE BE753091D patent/BE753091A/xx unknown
- 1970-07-08 JP JP45059433A patent/JPS5013798B1/ja active Pending
- 1970-07-08 HU HUCI001010 patent/HU162228B/hu unknown
- 1970-07-08 AR AR22989070A patent/AR193964A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| AR193964A1 (es) | 1973-06-12 |
| AT299450B (de) | 1972-06-26 |
| BE753091A (fr) | 1971-01-07 |
| HU162228B (https=) | 1973-01-29 |
| ES381471A2 (es) | 1973-01-16 |
| NL7010034A (https=) | 1971-01-12 |
| JPS5013798B1 (https=) | 1975-05-22 |
| CA921906A (en) | 1973-02-27 |
| FR2059491B1 (https=) | 1974-05-24 |
| FR2059491A1 (https=) | 1971-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |