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)
Abstract
1310046 Thiazacyclic amino compounds CIBA-GEIGY AG 2 July 1970 [8 July 1969 27 Nov 1969] 32141/70 Heading C2C The invention comprises the novel compounds 6 - amino - 2,2 - dimethyl - 3 - (2,2,2 - trichloroethoxy - carbonylamino) - penam, 6 - amino- 2,2 - dimethyl - 3 - 4 - methoxybenzyloxycarbonyl - amino) - penam, 6 - amino - 3 - (2- iodoethoxycarbonylamino) - 2,2 - dimethylpenam, and 3 - acetoxymethyl - 7 - amino - 4- (2,2,2 - trichloroethoxycarbonylamino) - ceph- (2)em, and a process for preparing these compounds and compounds of the formula wherein X is an etherified hydroxyl group, and R is a methylene group which may be substituted by one or two optionally substituted methyl groups, or a vinylene group which contains an optionally substituted methyl group attached to the carbon atom of the vinylene group which in the sulphur-nitrogen ring is exclusively bound to ring carbon atoms by reacting compounds of the formula in which Ac 0 is the acyl radical of an organic carboxylic acid, with acid halides capable of forming imide halides, converting the resulting imide halides into the corresponding imino ethers by treatment with alcohols and splitting the resulting imino ethers by treatment with a hydroxy compound, and, if desired, replacing in the resulting compounds having aliphatically bound chlorine or bromine atoms in the radical X, such Cl or Br atoms by treatment with iodine salts, and/or, if desired, resolving resulting isomer mixtures into single isomers. The following intermediates are prepared: 2,2 - dimethyl - 6 - (phenylacetylamino) - 3- (2,2,2 - trichloroethoxycarbonylamino)- penam, 2,2 - dimethyl - 6 - (phenylacetylamino)- penam- 3 - carboxylic acid azide, 3 - isocyanato - 2,2- dimethyl - 6 - (phenylacetyl - amino) - penam, 3 - (4 - benzyloxycarbonylamino)- 2,2 - dimethyl- 6 - (phenylacetylamino) - penam, 3 - (2 - iodoethoxycarbonylamino) - 2,2 - dimethyl - 6 - (phenylacetylamino) - penam, 3 - (2 - bromoethoxycarbonylamino) - 2,2 - dimethyl - 6 - (phenylacetylamino) - penam, 2,2 - dimethyl - 6 - (phenoxyacetylamino) - 3 - (2,2,2 - triohloroethoxycarbonylamino) - penam, penicillin - V - azide, 3 - isocyanato - 2,2 - dimethyl - 6 - (phenoxyacetylamino) - penam, 2,2 - dimethyl - 3 - (phenacyloxycarbonylamino)- 6 - (phenylacetylamino)- penam, 3 - acetoxymethyl - 7 - (2 - thienylacetylamino) - 4 - (2,2,2 - trichloroethoxycarbonylamino) - ceph(2)em, 6 - (tert - butoxycarbonylamino) - 2,2 - dimethyl - 3 - (2,2,2 - trichloroethoxycarbonylamino)- penam, 2,2 - dimethyl- 3 - (4 - methoxybenzyloxycarbonylamino)- 6- (phenoxyacetylamino)- penam, and 6 - (chlorocarbonylamino) - 2,2 - dimethyl - 3 - (2,2,2- trichloroethoxycarbonylamino)-penam,
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 (en) |
| AR (1) | AR193964A1 (en) |
| AT (1) | AT299450B (en) |
| BE (1) | BE753091A (en) |
| CA (1) | CA921906A (en) |
| ES (1) | ES381471A2 (en) |
| FR (1) | FR2059491B1 (en) |
| GB (1) | GB1310046A (en) |
| HU (1) | HU162228B (en) |
| NL (1) | NL7010034A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6058078U (en) * | 1983-09-30 | 1985-04-23 | 野田 弘 | incense holder |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1394820A (en) * | 1964-02-13 | 1965-04-09 | Ciba Geigy | New process for the preparation of amino compounds, in particular 7-amino-cephalosporanic acid |
| DE1935638A1 (en) * | 1968-07-23 | 1970-01-29 | Ciba Geigy | Acyloxyalkyl mercapto compounds |
| US3705160A (en) * | 1968-07-23 | 1972-12-05 | Ciba Geigy Corp | Thiazacyclic hydroxy compounds and process for their manufacture |
| DE1935640A1 (en) * | 1968-07-23 | 1970-03-05 | Ciba Geigy | Alkenyl mercapto compounds |
| DE1935970A1 (en) * | 1968-07-23 | 1970-01-29 | Ciba Geigy | Oxyacetic acid compounds |
| DE1935459A1 (en) * | 1968-07-23 | 1970-01-29 | Ciba Geigy | Carbinol alkyl mercapto compounds |
-
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/en not_active Expired
- 1970-07-07 BE BE753091D patent/BE753091A/en unknown
- 1970-07-07 NL NL7010034A patent/NL7010034A/xx unknown
- 1970-07-07 CA CA087472A patent/CA921906A/en not_active Expired
- 1970-07-07 AT AT613670A patent/AT299450B/en not_active IP Right Cessation
- 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/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AT299450B (en) | 1972-06-26 |
| HU162228B (en) | 1973-01-29 |
| BE753091A (en) | 1971-01-07 |
| FR2059491A1 (en) | 1971-06-04 |
| JPS5013798B1 (en) | 1975-05-22 |
| ES381471A2 (en) | 1973-01-16 |
| AR193964A1 (en) | 1973-06-12 |
| NL7010034A (en) | 1971-01-12 |
| FR2059491B1 (en) | 1974-05-24 |
| CA921906A (en) | 1973-02-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |